1,1'-Carbonyldiimidazole → N-(2-benzoyl-4-fluorophenyl)-1H-imidazole-1-carboxamide

HRID 19677

Reaction equation

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

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of (2-amino-5-fluorophenyl)(phenyl)methanone (6.60 g, 30.67 mmol) in CH2Cl2 (60 mL) was added carbonyldiimidazole (6.96 g, 42.93 mmol). The reaction was heated to 45° C. After 16 h at 45° C., the reaction was cooled to ambient temperature and the precipitate isolated by vacuum filtration and washed with fresh CH2Cl2 to give N-(2-benzoyl-4-fluorophenyl)-1H-imidazole-1-carboxamide as a white solid. 1H NMR (CDCl3, 400 MHz) 8.91 (s, NH); 7.47 (m, 3H, ArH); 7.25 (m, 1H, ArH); 7.18 (m, 4H, ArH); 6.99 (m, 1H, ArH); 6.95 (s, 1H, ArH); 6.53 (m, 1H, ArH); MS (Electrospray): m/z 332.1 (M+Na).

Workup

temperaturethe reaction was cooled to ambient temperature
customthe precipitate isolated by vacuum filtration
washwashed with fresh CH2Cl2

Sources & evidence

ORD record: ord-d74be2fba62443618bc212d24ff59743
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745452B2

Linked notes

Loading…