1,1-Dimethylhydrazine → Semicarbazide, 1,1-dimethyl-4-(o-(methoxycarbonyl)phenyl)-3-thio-

HRID 371624Notes

Reaction equation

HRID 371624 reaction equation
[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])=[C:2]=[S:3].[CH3:14][N:15]([CH3:17])[NH2:16]>C(O)C>[CH3:14][N:15]([CH3:17])[NH:16][C:2](=[S:3])[NH:1][C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 85243Benzoic acid, 2-isothiocyanato-, methyl ester

Product 1

HCID 3004929Semicarbazide, 1,1-dimethyl-4-(o-(methoxycarbonyl)phenyl)-3-thio-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 2-isothiocyanatobenzoate (6.0 g, prepared as described in J. Org. Chem., 1962, 27, 3701) and N,N-dimethylhydrazine (6 ml) in ethanol (60 ml) was stirred at room temperature for 1 hour. The precipitate was filtered off and dried to give methyl 2(3'-dimethylaminothioureido)benzoate (6.73 g, m.p. 149°-152°).

Workup

  1. filtrationThe precipitate was filtered off
  2. customdried

Sources & evidence

ORD record
ord-e681c3fbc6e94fd4b2921ea691f2a43b
Source dataset
uspto-grants-1978_05
Patent number
US04087422

Reaction notes

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