Dimethylformamide → N-cyano-N'-[2-(3-isothiazolylmethylthio)ethyl]-N"-methylguanidine

HRID 903748노트

반응식

HRID 903748 반응식
[N:1]#[C:2][NH2:3].[Pb].[CH3:5][NH:6][C:7]([NH:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[CH:18]=[CH:17][S:16][N:15]=1)=S.CN(C)C=O>C(#N)C>[C:2]([NH:3][C:7]([NH:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[CH:18]=[CH:17][S:16][N:15]=1)=[N:6][CH3:5])#[N:1]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 20466672N-Methyl-N'-(2-{[(1,2-thiazol-3-yl)methyl]sulfanyl}ethyl)thioureaHCID 22262466CH2N2Pb

생성물 1

HCID 9992541N-cyano-N'-[2-(3-isothiazolylmethylthio)ethyl]-N"-methylguanidine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Lead cyanamide (52.6 g.) was added to a solution of N-methyl-N'-[2-(3-isothiazolylmethylthio)ethyl]thiourea (17.7 g.) in acetonitrile (500 ml.) containing dimethylformamide (50 ml.). The mixture was stirred under reflux for 48 hours, then filtered and concentrated. The product was chromatographed on silica gel with ethyl acetate as eluant and recrystallised from isopropyl acetate-ether to give N-cyano-N'-[2-(3-isothiazolylmethylthio)ethyl]-N"-methylguanidine, in a crystalline form, m.p. 63°-64°. Further recrystallisation from isopropyl acetate afforded the cyanoguanidine in a crystalline form, m.p. 91°-92°. (Found: C, 42.6; H, 5.2; N, 27.4; S, 25.4. C9H13N5S2 requires: C, 42.3; H, 5.1; N, 27.4; S, 25.1).

후처리

  1. temperatureunder reflux for 48 hours
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe product was chromatographed on silica gel with ethyl acetate as eluant
  5. customrecrystallised from isopropyl acetate-ether

출처 및 근거

ORD 기록
ord-0f249f72dcde4127977435e80cf7275f
출처 데이터셋
uspto-grants-1980_10
특허 번호
US04228291

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