Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate → methyl 2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylate

HRID 892345Notes

Reaction equation

HRID 892345 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:5]([O:7][CH3:8])=[O:6].[C:13](NC(=NC(OC)=O)SC)(OC)=[O:14]>CN(C=O)C>[O:14]=[C:13]1[NH:12][C:11]2[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=2[NH:1]1

Participants

4

Reactant 2

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 1355243,5-Diamino-2-methylbenzoic acid

Product 1

HCID 10352553methyl 2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20 g (0.12 mol) of methyl 3,4-diaminobenzoate and 24.8 g (0.12 mol) of N,N'-dicarbomethoxy-S-methylisothiourea in 180 ml of DMF are heated under reflux for 4 hours. The DMF is then removed by distillation, the residue is vigorously stirred with water, and the crystals which have separated out are filtered off with suction and washed with water. After drying of the substance at 40° C. in vacuo, the product is suspended in acetone and then filtered off with suction.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe DMF is then removed by distillation
  3. customthe crystals which have separated out
  4. filtrationare filtered off with suction
  5. washwashed with water
  6. customAfter drying of the substance at 40° C. in vacuo
  7. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-43bb4a9658ea4a95aabb178fe1999f0f
Source dataset
uspto-grants-1992_06
Patent number
USRE033948

Reaction notes

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