4-Chlorobenzoyl chloride → HCID 67693640, compound

HRID 1417330Notes

Reaction equation

HRID 1417330 reaction equation
Cl.[N:2]1([C:7]2[CH:18]=[CH:17][C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:9][CH:8]=2)[CH:6]=[CH:5][N:4]=[CH:3]1.[OH-].[Na+].[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>O.C(OCC)C>[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][C:10]2[CH:17]=[CH:18][C:7]([N:2]3[CH:6]=[CH:5][N:4]=[CH:3]3)=[CH:8][CH:9]=2)=[O:27])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 14798Sodium HydroxideHCID 67598589HCID 67598589, compound

Product 1

HCID 67693640HCID 67693640, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2.8 g of 4-[4-(1H-imidazol-1-yl)phenoxy]butylamine hydrochloride (Example 2) in 50 ml of water is treated successively with 4 ml of 10N NaOH and 2.0 g of 4-chlorobenzoyl chloride in 100 ml of diethyl ether. Stirring at room temperature for 3 hours gives a precipitate which is collected, washed with diethylether and water, and air dried. Recrystallization from 33% aqueous ethanol gives the desired product, m.p. 138°-139° C.; yield, 1.3 g.

Workup

  1. customgives a precipitate which
  2. customis collected
  3. washwashed with diethylether and water, and air
  4. customdried
  5. customRecrystallization from 33% aqueous ethanol

Sources & evidence

ORD record
ord-bbddc911960b4ed692ae63366dc733ec
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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