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

HRID 27539Notes

Reaction equation

HRID 27539 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-61a3b53682664ccd86b5d0db0ea473d8
Source dataset
uspto-grants-1980_09
Patent number
US04221802

Reaction notes

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