N-[(2-chlorophenyl)methyl]-2-cyanoacetamide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: As for Example 1, N-o-chlorobenzyl-2-cyanoacetamide, colorless needles, m.p. 108°-109° C., (prepared as described in U.S. Pat. No. 3,116,312) is heated with N,N-dimethylformamide dimethylacetal to give N-o-chlorobenzyl-2-cyano-3-dimethylaminoacrylamide as colorless needles, m.p. 144°-146.5° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of N-(2'-chlorobenzyl)-2-cyanoacetamide 179 g. (0.86 mole) and 2,4-pentanedione 86 g. (0.86 mole) in 500 ml. of 95% ethanol containing 10 ml. of piperidine is refluxed for 24 hours, after cooling the white crystalline product is isolated by vacuum filtration washed with ether and dried in vacuo to give 237.3 g. (87% yield) mp>250° C.;ν2210 (CN) and 1650 cm.-1 (C=O). after cooling the white crystalline product is isolated by vacuum filtration washed with ether dried in vacuo to give 237.3 g

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of N-(2'-chlorobenzyl)-2-cyanoacetamide 179 g. (0.86 mole) and 2,4-pentanedione 86 g. (0.86 mole) in 500 ml. of 95% ethanol containing 10 ml. of piperidine is refluxed for 24 hours, after cooling the white crystalline product is isolated by vacuum filtration washed with ether and dried in vacuo to give 237.3 g. (87% yield) mp>250° C.;ν2210 (CN) and 1650 cm.-1 (C=O). after cooling the white crystalline product is isolated by vacuum filtration washed with ether dried in vacuo to give 237.3 g

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 80.5 g. (0.71 mole) of ethyl cyanoacetate and 100 g. (0.71 mole) of 2-chlorobenzylamine in 200 ml. of absolute ethanol heated at reflux for 2 hours and then allowed to stand at ambient temperature overnight. The solvent is removed in vacuo and the residue is recrystallized from ether/pentane to give 56 g. (38% yield) of the desired product as a near white solid, m.p. 102°-4° C.;ν3300 (NH), 2270 (CN), and 1650 cm.-1 (C=O);δ8.7 (broad, 1H, NH), 7.35 (broad s, 4H, aromatic protons), 4.40 (d, 2H, benzyl methylene) and 3.7 (broad s, 2H, CH2CO). at reflux for 2 hours The solvent is removed in vacuo the residue is recrystallized from ether/pentane to give 56 g

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of N-(2'-chlorobenzyl)-2-cyanoacetamide 179 g. (0.86 mole) and 2,4-pentanedione 86 g. (0.86 mole) in 500 ml. of 95% ethanol containing 10 ml. of piperidine is refluxed for 24 hours, after cooling the white crystalline product is isolated by vacuum filtration washed with ether and dried in vacuo to give 237.3 g. (87% yield) mp>250° C.;ν2210 (CN) and 1650 cm.-1 (C= O). after cooling the white crystalline product is isolated by vacuum filtration washed with ether dried in vacuo to give 237.3 g

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of N-(2'-chlorobenzyl)-2-cyanoacetamide 179 g. (0.86 mole) and 2,4-pentanedione 86 g. (0.86 mole) in 500 ml. of 95% ethanol containing 10 ml. of piperidine is refluxed for 24 hours, after cooling the white crystalline product is isolated by vacuum filtration washed with ether and dried in vacuo to give 237.3 g. (87% yield) mp>250° C.;ν2210 (CN) and 1650 cm.-1 (C= O). after cooling the white crystalline product is isolated by vacuum filtration washed with ether dried in vacuo to give 237.3 g

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 80.5 g. (0.71 mole) of ethyl cyanoacetate and 100 g. (0.71 mole) of 2-chlorobenzylamine in 200 ml. of absolute ethanol heated at reflux for 2 hours and then allowed to stand at ambient temperature overnight. The solvent is removed in vacuo and the residue is recrystallized from ether/pentane to give 56 g. (38% yield) of the desired product as a near white solid, m.p. 102°-4° C.; ν3300 (NH), 2270 (CN), and 1650 cm.-1 (C= O); δ 8.7 (broad, 1H, NH), 7.35 (broad s, 4H, aromatic protons), 4.40 (d, 2H, benzyl methylene) and 3.7 (broad s, 2H, CH2CO). at reflux for 2 hours The solvent is removed in vacuo the residue is recrystallized from ether/pentane to give 56 g

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: As for Example 1, N-o-chlorobenzyl-2-cyanoacetamide, colorless needles, m.p. 108°-109° C., (prepared as described in U.S. Pat. No. 3,116,312) is heated with N,N-dimethylformamide dimethylacetal to give N-o-chlorobenzyl-2-cyano-3-dimethylaminoacrylamide as colorless needles, m.p. 144°-146.5° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of N-(2'-chlorobenzyl)-2-cyanoacetamide 179 g. (0.86 mole) and 2,4-pentanedione 86 g. (0.86 mole) in 500 ml. of 95% ethanol containing 10 ml. of piperidine is refluxed for 24 hours, after cooling the white crystalline product is isolated by vacuum filtration washed with ether and dried in vacuo to give 237.3 g. (87% yield) mp>250° C.;ν2210 (CN) and 1650 cm.-1 (C=O). after cooling the white crystalline product is isolated by vacuum filtration washed with ether dried in vacuo to give 237.3 g

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 80.5 g. (0.71 mole) of ethyl cyanoacetate and 100 g. (0.71 mole) of 2-chlorobenzylamine in 200 ml. of absolute ethanol heated at reflux for 2 hours and then allowed to stand at ambient temperature overnight. The solvent is removed in vacuo and the residue is recrystallized from ether/pentane to give 56 g. (38% yield) of the desired product as a near white solid, m.p. 102°-4° C.;ν3300 (NH), 2270 (CN), and 1650 cm.-1 (C=O);δ8.7 (broad, 1H, NH), 7.35 (broad s, 4H, aromatic protons), 4.40 (d, 2H, benzyl methylene) and 3.7 (broad s, 2H, CH2CO). at reflux for 2 hours The solvent is removed in vacuo the residue is recrystallized from ether/pentane to give 56 g