2-Amino-5-chlorobenzophenone → N-(2-benzoyl-4-chlorophenyl)-1H-imidazole-1-carboxamide

HRID 19672Notes

Reaction equation

HRID 19672 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[C:17](N1C=CN=C1)([N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1)=[O:18]>C(Cl)Cl>[C:4]([C:3]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:2]=1[NH:1][C:17]([N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1)=[O:18])(=[O:5])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 128702-Amino-5-chlorobenzophenoneHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 21755276N-(2-benzoyl-4-chlorophenyl)-1H-imidazole-1-carboxamideYield 69.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 2-amino-5-chlorobenzophenone (40 g, 172.7 mmol) in CH2Cl2 (175 μL) was added carbonyldiimidazole (30.8 g, 189.9 mmol). The reaction was heated to 45° C. for 16 h resulting in a white precipitate. The reaction was cooled in an ice bath and the precipitate collected by vacuum filtration and dried to give 39.3 g (69.9%) of N-(2-benzoyl-4-chlorophenyl)-1H-imidazole-1-carboxamide as a white solid. 1H NMR (CDCl3, 400 MHz) 8.66 (s, 1H); 7.46 (m, 4H); 7.25 (s, 1H); 7.19 (d, J=6.96 Hz, 2H); 7.15 (s, 1H); 6.94 (m, 2H); 6.76 (d, J=2.29 Hz, 1H). MS (Electrospray): m/z 348.0 (M+Na).

Workup

  1. customresulting in a white precipitate
  2. temperatureThe reaction was cooled in an ice bath
  3. filtrationthe precipitate collected by vacuum filtration
  4. customdried

Sources & evidence

ORD record
ord-89b47f21b7964839ac20d179765c75c8
Source dataset
uspto-grants-2010_06
Patent number
US07745452B2

Reaction notes

Loading…