4-Bromobenzoyl chloride → HCID 67693663, compound

HRID 1417332Notes

Reaction equation

HRID 1417332 reaction equation
[N:1]1([C:6]2[CH:18]=[CH:17][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[Br:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>ClCCl.[OH-].[Na+]>[Br:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:9]2[CH:17]=[CH:18][C:6]([N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[CH:7][CH:8]=2)=[O:25])=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 685154-Bromobenzoyl chlorideHCID 54243064HCID 54243064, compound

Product 1

HCID 67693663HCID 67693663, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2.9 g of 5-[4-(1H-imidazol-1-yl)phenoxy]pentaneamine (Example 27) in 150 ml of dichloromethane and 100 ml 1N NaOH are combined and stirred vigorously as 2.8 g of 4-bromobenzoyl chloride is added. The reaction mixture is stirred at room temperature for 20 hours, the dichloromethane layer separated and dried over Na2SO4. The dichloromethane solution is diluted with 200 ml of hexane, and the solution concentrated to turbidity. Cooling the mixture at room temperature gives the desired product as white crystals, m.p. 150°-151° C.; yield, 1.4 g.

Workup

  1. additionis added
  2. customthe dichloromethane layer separated
  3. dry with materialdried over Na2SO4
  4. additionThe dichloromethane solution is diluted with 200 ml of hexane
  5. concentrationthe solution concentrated to turbidity
  6. temperatureCooling the mixture at room temperature

Sources & evidence

ORD record
ord-8af1169ad9ec40c8b1b3bf6d00a29c57
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

Loading…