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

HRID 2417689

반응식

HRID 2417689 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 72391,2-Dichlorobenzene용매

반응 조건

온도
120 °C

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-98c4bf982f764d9eb1df99f8d49cec75
출처 데이터셋
uspto-grants-1984_09
특허 번호
US04469868

연결된 노트

불러오는 중…