Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate → HCID 178502036, compound

HRID 1823778Notes

Reaction equation

HRID 1823778 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[NH2:8].[CH3:27][O:28][C:29]([NH:31][C:32](=NC(OC)=O)SC)=[O:30]>C(O)(=O)C.CO>[CH3:27][O:28][C:29]([NH:31][C:32]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([O:9][S:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[CH:15][CH:14]=3)(=[O:12])=[O:11])=[CH:3][C:2]=2[N:1]=1)=[O:30]

Participants

5

Reactant 2

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 87767950HCID 87767950, compound

Product 1

HCID 178502036HCID 178502036, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 4-benzyloxy-benzenesulfonic acid 3,4-diamino-phenyl ester (134 mg) in acetic acid (0.83 ml) and methanol (2.5 ml) at 80° C. was added 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (89 mg). The reaction mixture was refluxed for 2 hours then allowed to cool to ambient temperature and stirred at this temperature for 14 hours. The resultant precipitate was filtered, washed with diethyl ether and dried under vacuum to afford 4-benzyloxy-benzenesulfonic acid 2-methoxycarbonylamino-1H-benzoimidazol-5-yl ester as a beige solid. Mass spectrum: 454 [M+H]+; retention time=11.46 minutes.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. filtrationThe resultant precipitate was filtered
  3. washwashed with diethyl ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-08ad16973a4a483284f8600838b6adb5
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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