Phosgene → 1-cyclobutyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester

HRID 1828186Notes

Reaction equation

HRID 1828186 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:14][CH2:13][CH2:12]2)=[C:6]([NH2:15])[CH:5]=1.[C:17](Cl)(Cl)=[O:18]>ClCCl.C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH:11]3[CH2:14][CH2:13][CH2:12]3)[C:17](=[O:18])[NH:15][C:6]=2[CH:5]=1)=[O:16]

Participants

6

Reactant 2

HCID 6371PhosgeneHCID 62414059HCID 62414059, compound

Product 1

HCID 695855151-cyclobutyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-4-cyclobutylamino-benzoic acid methyl ester (15.94 g, 72.3 mmol) in dichloromethane (250 ml) at 23 C was added phosgene (38.3 ml of a 20% solution in toluene) dropwise over 30 minutes. The reaction was allowed to stand for 2 hours then was diluted with water and extracted with ethyl acetate. The organic layer was dried with sodium sulfate and concentrated in vacuo to give 17.01 g of 1-cyclobutyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce12e066ce3e453b9a1601b3222c8459
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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