Hydrochloride methanol → (2-Amino-5-chlorophenyl)(4-bromophenyl)methanone

HRID 19692Notes

Reaction equation

HRID 19692 reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[NH:15]C(=O)OC(C)(C)C)=[O:7])=[CH:4][CH:3]=1.Cl.CO>CO>[NH2:15][C:9]1[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:8]=1[C:6]([C:5]1[CH:23]=[CH:24][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:7]

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 59346594Tert-butyl[2-(4-bromobenzoyl)-4-chlorophenyl]carbamate

Product 1

HCID 12295793(2-Amino-5-chlorophenyl)(4-bromophenyl)methanoneYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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. customThe organic layer was evaporated
  2. customthe residue was partitioned between CH2Cl2 (300 ml) and water (200 ml)
  3. washThe organic layer was washed with 10% Na2CO3 (to pH=9) and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-df54a81bd19d4c4fa9662af4c20a77e9
Source dataset
uspto-grants-2010_06
Patent number
US07745452B2

Reaction notes

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