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

HRID 1493185ノート

反応式

HRID 1493185 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dd218aad07284402a56b77548753f26c
出典データセット
uspto-grants-1991_06
特許番号
US05021429

反応ノート

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