Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate → HCID 178502035, compound

HRID 1823782Notes

Reaction equation

HRID 1823782 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][CH2:20][CH:21]3[CH2:23][CH2:22]3)=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[NH2:8].[CH3:24][O:25][C:26]([NH:28][C:29](=NC(OC)=O)SC)=[O:27]>C(O)(=O)C.CO>[CH3:24][O:25][C:26]([NH:28][C:29]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]([NH:19][CH2:20][CH:21]4[CH2:22][CH2:23]4)=[CH:15][CH:14]=3)(=[O:12])=[O:11])=[CH:3][C:2]=2[N:1]=1)=[O:27]

Participants

5

Reactant 2

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 865960794-(Cyclopropylmethyl-amino)-benzenesulfonic acid 3,4-diamino-phenyl ester

Product 1

HCID 178502035HCID 178502035, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 4-(cyclopropylmethyl-amino)-benzenesulfonic acid 3,4-diamino-phenyl ester (648 mg) in acetic acid (4.5 ml) and methanol (40 ml) at 80° C. was added 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (580 mg). The reaction mixture was refluxed for 4 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-(cyclopropylmethyl-amino)-benzene sulfonic acid 2-methoxycarbonylamino-1H-benzoimidazol-5-yl ester (378 mg) as a beige solid. Mass spectrum: 417 [M+H]+; retention time=13.16 minutes.

Workup

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

Sources & evidence

ORD record
ord-30c39d20c91f45fb8dc98fc8366c8ac4
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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