Sodium hydride → 5-Amino-1-(4-cyano-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide

HRID 1194721ノート

反応式

HRID 1194721 の反応式
[NH2:1][C:2]1[NH:6][N:5]=[N:4][C:3]=1[C:7]([NH2:9])=[O:8].[H-].[Na+].[C:12]([C:14]1[C:21]([Cl:22])=[CH:20][C:17]([CH2:18]Cl)=[CH:16][C:15]=1[Cl:23])#[N:13]>CN(C)C=O>[NH2:1][C:2]1[N:6]([CH2:18][C:17]2[CH:16]=[C:15]([Cl:23])[C:14]([C:12]#[N:13])=[C:21]([Cl:22])[CH:20]=2)[N:5]=[N:4][C:3]=1[C:7]([NH2:9])=[O:8]

参加物

5

反応物 3

HCID 24758Sodium hydride2 回HCID 230362434-Cyano-3,5-dichlorobenzyl chlorideHCID 178513860HCID 178513860、化合物

生成物 1

HCID 140330315-Amino-1-(4-cyano-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide収率 23.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A stirred, ambient temperature solution of 5-amino-1,2,3-triazole-4-carboxamide (630 mg, 5.0 mmol) in dry N,N-dimethylformamide (20 ml) was treated with sodium hydride (250 mg of a 50% dispersion in mineral oil, 125 mg NaH, 5.2 mmol). The resulting suspension was stirred 10 min., 4-cyano-3,5-dichlorobenzyl chloride (1.1 g, 5.0 mmol) was added, and the mixture was stirred 2 hours. The reaction was quenched by pouring into ice and water (80 ml). The suspension was filtered and washed three times with water. The solid was suspended in 19:1 (v/v) dichloromethane-methanol and filtered to provide 364 mg (23%) 5-amino-1-(4-cyano-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide. Recrystallization from ethanol provided material of m.p 238°-239.5° C.

後処理

  1. stirringthe mixture was stirred 2 hours
  2. customThe reaction was quenched
  3. additionby pouring into ice and water (80 ml)
  4. filtrationThe suspension was filtered
  5. washwashed three times with water
  6. filtrationfiltered

出典と根拠

ORDレコード
ord-21702f4c6a934a54bc6e4f70b1cf0177
出典データセット
uspto-grants-1989_03
特許番号
US04816469

反応ノート

読み込み中…