Water → HCID 22714359, compound

HRID 564837Notes

Reaction equation

HRID 564837 reaction equation
[C:1](Cl)(=O)[C:2]1C=CC=C[CH:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)([OH:24])[C:18]2[N:22]([CH3:23])[CH:21]=[N:20][CH:19]=2)=[CH:13][C:12]=1[C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=1)=[O:33].N1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[OH2:47]>C(Cl)Cl>[Cl:40][C:36]1[CH:35]=[C:34]([CH:39]=[CH:38][CH:37]=1)[C:32]([C:12]1[CH:13]=[C:14]([C:17]([C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)([OH:24])[C:18]2[N:22]([CH3:23])[CH:21]=[N:20][CH:19]=2)[CH:15]=[CH:16][C:11]=1[NH:10][C:42](=[O:47])[CH2:43][C:44]1[CH:3]=[CH:2][CH:1]=[CH:46][CH:45]=1)=[O:33]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 22714353HCID 22714353, compound

Product 1

HCID 22714359HCID 22714359, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of benzoyl chloride (3.1 ml) in DCM (25 ml) was added dropwise at room temperature to a solution of interm. (6-d) (7 g) and pyridine (5 ml) in DCM (70 ml). The mixture was stirred at room temperature for 45 minutes. Water was added and the mixture was decanted. The organic layer was dried (MgSO4), filtered and the solvent was evaporated, yielding 8.8 g of (±)-N-[2-(3-chlorobenzoyl)-4-[(4-chlorophenyl)-hydroxy(1-methyl-1H-imidazol-5-yl)methyl]phenyl]benzeneacetamide (interm. 7). The product was used without further purification.

Workup

  1. additionwas added dropwise at room temperature to a solution of interm
  2. customthe mixture was decanted
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cfd50119284c463d8e073b80621b8d21
Source dataset
uspto-grants-2001_01
Patent number
US06169096A

Reaction notes

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