Triethylamine → 5-Cyano-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester

HRID 1643944Notes

Reaction equation

HRID 1643944 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][C:9]=1[NH2:16])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:26](Cl)([O:28]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[C:1]([O:5][C:6]([N:7]1[C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][C:9]=2[NH:16][C:26]1=[O:28])=[O:17])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 667547631,1-Dimethylethyl N-(2-amino-4-cyanophenyl)carbamate

Product 1

HCID 249009585-Cyano-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl esterYield 204.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a chilled solution of (2-amino-4-cyanophenyl)-carbamic acid tert-butyl ester (2.1 g, 8.8 mmol) in CH2Cl2 (50 mL) and triethylamine (1.22 mL, 8.8 mmol) was added a solution of triphosgene (0.94 g, 3.2 mmol) in CH2Cl2 (50 mL) slowly. The reaction was stirred at room temperature for 3 hours, diluted with CH2Cl2, washed with water, brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography in silica gel using a gradient from 30% to 60% ethyl acetate in n-heptane as eluent to afford 5-cyano-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester (1.7 g, 75%) as a white solid.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography in silica gel using a gradient from 30% to 60% ethyl acetate in n-heptane as eluent

Sources & evidence

ORD record
ord-38e38bddd0e443f2a82c9259a85cf125
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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