Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate → HCID 178502026, compound

HRID 2261952Notes

Reaction equation

HRID 2261952 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[NH2:26])[C:5]([C:7]1[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=1[C:9]([O:11]CC1C=CC=CC=1)=O)=[O:6].[CH3:27][O:28][C:29]([NH:31][C:32](=NC(OC)=O)SC)=[O:30]>C(O)(=O)C>[CH3:27][O:28][C:29](=[O:30])[NH:31][C:32]1[NH:26][C:25]2[CH:24]=[CH:23][C:4]([C:5](=[O:6])[C:7]3[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=3[C:9]([CH2:5][C:4]3[CH:23]=[CH:24][CH:25]=[CH:2][CH:3]=3)=[O:11])=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 67044774Benzyl 2-(3,4-diaminobenzoyl)benzoate

Product 1

HCID 178502026HCID 178502026, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of benzyl 2-(3,4-diaminobenzoyl)benzoate (25 g, 72 mmole) and 1,3-bis(methoxy carbonyl)-2-methyl-2-thiopseudourea (19.3 g, 94 mmole) in acetic acid (100 ml) was heated to 75° C. for 45 minutes. The solution was cooled to room temperature and concentrated in-vacuo. The resultant oil was diluted in ethyl acetate (300 mL) and washed with 1N sodium hydroxide (200 mL), water (2×200 mL), dried over sodium sulfate, filtered and concentrated in-vacuo. The resultant solid was re-crystallized using ethyl ether and ethyl acetate (2:1). The solid was isolated by vacuum filtration and washed ethyl ether to afford [5-(2-benzylcarbanoyl-benzoyl)-1H-benzoimidazol-2-yl]-carbamic acid methyl ester, 21.4 g, 49.8 mmol, (69%) as a yellow solid. 1H NMR (400 MHz, d6-DMSO): 8.04 (br s, 1H), 7.77-7.68 (m, 3H), 7.52-7.41 (m, 3H), 7.28-7.10 (m, 5H), 5.05 (s, 2H), 3.76 (s, 3H); MS (EI) for C24H20N4O4: 430 (MH+)

Workup

  1. concentrationconcentrated in-vacuo
  2. additionThe resultant oil was diluted in ethyl acetate (300 mL)
  3. washwashed with 1N sodium hydroxide (200 mL), water (2×200 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in-vacuo
  7. customThe resultant solid was re-crystallized
  8. customThe solid was isolated by vacuum filtration
  9. washwashed ethyl ether

Sources & evidence

ORD record
ord-d8f79071e7af4959ab900f9756306dfe
Source dataset
uspto-grants-2010_12
Patent number
US07846959B2

Reaction notes

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