4-Chlorobenzoyl chloride → HCID 23453102, compound

HRID 1277669Notes

Reaction equation

HRID 1277669 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[NH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:28])([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:27])([CH3:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 20463387HCID 20463387, compound

Product 1

HCID 23453102HCID 23453102, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

9.6 g. 4-Chlorobenzoyl chloride are added dropwise to a solution of 14.1 g ethyl 2-[4-(2-aminoethyl)-phenyl]-2-methylpropionate hydrochloride in 90 ml anhydrous pyridine at 5°-10° C. The reaction mixture is kept at 10° C. for 90 minutes, then allowed to warm up to ambient temperature and subsequently heated to 45° C. for 10 minutes. A part thereof remains undissolved. The reaction mixture is stirred into 750 ml. ice water, filtered with suction and the filter cake then washed. There are obtained 13.2 g (68% of theory) ethyl 2-{4-[2-(4-chlorobenzamido)-ethyl]-phenyl}-2-methylpropionate which, after recrystallization from isopropanol, melts at 108°-109° C.

Workup

  1. temperaturesubsequently heated to 45° C. for 10 minutes
  2. filtrationice water, filtered with suction
  3. washthe filter cake then washed

Sources & evidence

ORD record
ord-f6a50e548673405a8c57123657410562
Source dataset
uspto-grants-1981_07
Patent number
US04278680

Reaction notes

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