Water → N-[4-chloro-2-(4-bromobenzoyl)phenyl]-1H-imidazole-1-carboxamide

HRID 19693Notes

Reaction equation

HRID 19693 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)=[O:10].[C:18](N1C=CN=C1)([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)=[O:19].CCOCC.O>C(Cl)Cl>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:18]([N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)=[O:19])=[C:3]([C:9](=[O:10])[C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 682631,1'-CarbonyldiimidazoleHCID 12295793(2-Amino-5-chlorophenyl)(4-bromophenyl)methanone

Product 1

HCID 59346584N-[4-chloro-2-(4-bromobenzoyl)phenyl]-1H-imidazole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl [2-(4-bromobenzoyl)-4-chlorophenyl]carbamate (10 g, 25 mmol) in MeOH (50 mL) at 25° C. was added 2 M HCl-MeOH (100 ml), and the reaction mixture stirred for 4 h. The organic layer was evaporated, then the residue was partitioned between CH2Cl2 (300 ml) and water (200 ml). The organic layer was washed with 10% Na2CO3 (to pH=9) and brine, dried over Na2SO4 and evaporated to give 7.5 g (98% yield) (2-amino-5-chlorophenyl)(4-bromophenyl)methanone. To a solution of (2-amino-5-chlorophenyl)(4-bromophenyl)methanone (13 g, 42 mmol) in 500 ml CH2Cl2 was added solid carbonyldiimidazole (15.7 g, 96 mmol) portionwise. The resulting yellow solution was allowed to stir at 40° C. for 16 hrs, concentrated to give a yellow foam. The foam was treated with 30 ml of ether and 20 ml of water with vigorous stirring resulting in a solid precipitate. After filtration, the cake was recrystallized from CH2Cl2/Ether (1:5) to give N-[4-chloro-2-(4-bromobenzoyl)phenyl]-1H-imidazole-1-carboxamide as a yellow solid. 1HNMR: (400 MHz, DMSO-d6) δ 11.05 (s, 1H), 7.69 (d, J=8.4 Hz, 2H), 7.55 (dd, J=8.4, 1.6 Hz, 1H), 7.33 (s, 1H), 6.98˜7.10 (m, 5H), 6.71 (d, J=2.0 Hz, 1H).

Workup

  1. concentrationconcentrated
  2. customto give a yellow foam
  3. stirringwith vigorous stirring
  4. customresulting in a solid precipitate
  5. filtrationAfter filtration
  6. customthe cake was recrystallized from CH2Cl2/Ether (1:5)

Sources & evidence

ORD record
ord-050017df70ba47d185b4fd5fb677e6e4
Source dataset
uspto-grants-2010_06
Patent number
US07745452B2

Reaction notes

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