Acetonitrile → N-Methyl-N'-[2-[[3-(N,N-dimethylaminomethyl)phenyl]methylthio]ethyl]-2-nitro-1,1-ethenediamine

HRID 1493185노트

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HRID 1493185 반응식
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][NH2:15])[CH:8]=[CH:9][CH:10]=1)[CH3:3].[N+:16]([CH:19]=[C:20](SC)SC)([O-:18])=[O:17].[C:25](#[N:27])C>>[CH3:25][NH:27][C:20]([NH:15][CH2:14][CH2:13][S:12][CH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH:6]=1)=[CH:19][N+:16]([O-:18])=[O:17]

참가 물질

4

반응물 3

HCID 6342AcetonitrileHCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 129520192-[[3-(N,N-Dimethylaminomethyl)phenyl]methylthio]ethanamine

생성물 1

HCID 67946713N-Methyl-N'-[2-[[3-(N,N-dimethylaminomethyl)phenyl]methylthio]ethyl]-2-nitro-1,1-ethenediamine

실험 절차

2-[[3-(N,N-Dimethylaminomethyl)phenyl]methylthio]ethanamine (3 g) and 1-nitro-2,2-bis(methylthio)ethylene (2.2 g) were heated under reflux in acetonitrile for 7 hours. The solvent was removed and the residual oil used without further purification. The oil was treated with ethanolic methylamine (33%, 34 ml) and heated under reflux for 3 hours. The solvent was removed and the residual oil was purified by column chromatography on silica with methanol. The resultant orange oil was triturated with ether to give the title compound as a white crystalline solid (0.23 g) m.p. 62°-4°. TLC silica; ethyl acetate:isopropanol:water:0.88 ammonia (25:15:8:2) Rf 0.36.

후처리

  1. customThe solvent was removed
  2. customthe residual oil used without further purification
  3. additionThe oil was treated with ethanolic methylamine (33%, 34 ml)
  4. temperatureheated
  5. temperatureunder reflux for 3 hours
  6. customThe solvent was removed
  7. customthe residual oil was purified by column chromatography on silica with methanol
  8. customThe resultant orange oil was triturated with ether

출처 및 근거

ORD 기록
ord-dd218aad07284402a56b77548753f26c
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05021429

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