Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate → HCID 178502048, compound

HRID 616915Notes

Reaction equation

HRID 616915 reaction equation
[CH3:1][CH:2]([CH3:14])[CH2:3][S:4]([C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([NH2:13])[CH:7]=1)=[O:5].[CH3:15][O:16][C:17]([NH:19][C:20](=NC(OC)=O)SC)=[O:18]>CO.C(O)(=O)C>[CH3:1][CH:2]([CH3:14])[CH2:3][S:4]([C:6]1[CH:11]=[CH:10][C:9]2[NH:12][C:20]([NH:19][C:17](=[O:18])[O:16][CH3:15])=[N:13][C:8]=2[CH:7]=1)=[O:5]

Participants

5

Reactant 2

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 203669674-(2-Methylpropane-1-sulfinyl)benzene-1,2-diamine

Product 1

HCID 178502048HCID 178502048, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To 3.09 g (14.5 mMol) of 4-(2-methylpropyl)sulfinyl-1,2-diaminobenzene in 35 ml methanol and 0.84 ml acetic acid is added 3.11 g (16 mMol) 1,3-bis(methoxycarbonyl)-S-methyl isothiourea, prepared as described in Example 1A(5), and the resulting solution heated to reflux for 3 hours. The solvent is removed in vacuo, the solid digested with water and filtered and washed with ether. The resulting orange solid is recrystallized from 35 ml ethanol to yield 3.0 g of the title compound, m.p. 198°-201°, yield, 70%.

Workup

  1. customprepared
  2. temperaturethe resulting solution heated
  3. temperatureto reflux for 3 hours
  4. customThe solvent is removed in vacuo
  5. filtrationthe solid digested with water and filtered
  6. washwashed with ether
  7. customThe resulting orange solid is recrystallized from 35 ml ethanol

Sources & evidence

ORD record
ord-55d55a6cb1a14d86927cdda6406d04fd
Source dataset
uspto-grants-1978_02
Patent number
US04076825

Reaction notes

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