Propylenediamine → 2-(1,3-Dimethyl-4-nitropyrazol-5-yl)-4-methylimidazoline

HRID 2417689

反応式

HRID 2417689 の反応式
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:13][CH2:14][CH:15](N)[CH3:16].[C:18]([C:20]1[N:24]([CH3:25])[N:23]=[C:22]([CH3:26])[C:21]=1[N+:27]([O-:29])=[O:28])#[N:19]>ClC1C=CC=CC=1Cl>[CH3:25][N:24]1[C:20]([C:18]2[NH:13][CH2:14][CH:15]([CH3:16])[N:19]=2)=[C:21]([N+:27]([O-:29])=[O:28])[C:22]([CH3:26])=[N:23]1

参加物

5

反応物 3

HCID 6567PropylenediamineHCID 965071,3-dimethyl-4-nitro-1H-pyrazole-5-carbonitrileHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 1784340142-(1,3-Dimethyl-4-nitropyrazol-5-yl)-4-methylimidazoline収率 84.3%

試薬・触媒・溶媒 1

HCID 72391,2-Dichlorobenzene溶媒

反応条件

温度
120 °C

実験手順

p-Toluenesulfonic acid monohydrate (15.2 g, 0.08 mol) is added in portions with stirring to 6 g (0.08 mol) of 1,2-diaminopropane under nitrogen. To the resulting melt (ca 100° C.) is added in portions 12.6 g (0.076 mol) of 5-cyano-1,3-dimethyl-4-nitropyrazole (mp 93° C.); the mixture is stirred and heated to 120° C. and 25 ml of o-dichlorobenzene is added; stirring is continued at 120°-130° for 0.5 hours then at 160° C. for three hours. The cooled mixture is extracted with 75 ml of 3N HCl. The aqueous extract is made strongly basic with a large excess of concentrated NH4OH and the mixture is extracted thoroughly with methylene dichloride. Evaporation of the extract gives 14.3 g (84%) of 2-(1,3-dimethyl-4-nitropyrazol-5-yl)-4-methylimidazoline, mp 98°-101°.

後処理

  1. stirringstirring
  2. waitat 160° C. for three hours
  3. extractionThe cooled mixture is extracted with 75 ml of 3N HCl
  4. extractionThe aqueous extract
  5. extractionthe mixture is extracted thoroughly with methylene dichloride
  6. customEvaporation of the extract

出典と根拠

ORDレコード
ord-98c4bf982f764d9eb1df99f8d49cec75
出典データセット
uspto-grants-1984_09
特許番号
US04469868

関連ノート

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