Ethyl Acetate → HCID 69019837, compound

HRID 860779Notes

Reaction equation

HRID 860779 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)([OH:20])[C:14]2[N:18]([CH3:19])[CH:17]=[N:16][CH:15]=2)=[CH:9][C:8]=1[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=1)=[O:29].CCOC(C)=O.[OH-].[Na+]>C(O)(=O)C>[Br:1][CH2:2][C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)([OH:20])[C:14]2[N:18]([CH3:19])[CH:17]=[N:16][CH:15]=2)=[CH:9][C:8]=1[C:28](=[O:29])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=1)=[O:4]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 61147Bromoacetyl bromideHCID 22714353HCID 22714353, compound

Product 1

HCID 69019837HCID 69019837, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromo-acetyl bromide (0.0138 mol) was added slowly at 5° C. to a mixture of (±)-[2-amino-5-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]phenyl](3-chlorophenyl)methanone (prepared as described in WO 97/21701) (0.0137 mol) in acetic acid (60 ml). The mixture was stirred for 15 min and poured out into EtOAc and NaOH 0.5N. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated till dryness, yielding 7.3 g (93%) of 2-bromo-N-[2-(3-chlorobenzoyl)-4-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]phenyl]-acetamide (intermediate 4).

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated till dryness

Sources & evidence

ORD record
ord-056b55f2913f4c82a2a3111791c7234d
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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