Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate → HCID 178502034, compound

HRID 1823775Notes

Reaction equation

HRID 1823775 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[NH2:8].[CH3:10][O:11][C:12]([NH:14][C:15](=NC(OC)=O)SC)=[O:13]>CO.C(O)(=O)C>[CH3:10][O:11][C:12](=[O:13])[NH:14][C:15]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([OH:9])=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 2

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 27729703,4-Diaminophenol

Product 1

HCID 178502034HCID 178502034, compoundYield 109.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

6 g of 3,4-diaminophenol were combined with 9.8 g of 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea in 50 ml methanol and 30 ml acetic acid. The reaction mixture was refluxed for 4 hours. Solvents were then evaporated under reduce pressure yielding 10.8 g crude (5-hydroxy-1H-benzoimidazol-2-yl)-carbamic acid methyl ester. The residue was subjected to flash chromatography eluting with a mixture of dichloromethane-methanol (9:1; v/v) to give 5.6 g of a beige solid. Mass spectrum: 208 [M+H]+, retention time=0.56 minute.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. customSolvents were then evaporated

Sources & evidence

ORD record
ord-15947990423647cfb58259068c63361f
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

Loading…