4-Chlorobenzoyl chloride → HCID 3367087, compound

HRID 1277660Notes

Reaction equation

HRID 1277660 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1>[OH-].[Na+].CC(C)=O.O>[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=2)=[O:18])=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 145334-Aminophenylacetic acid

Product 1

HCID 3367087HCID 3367087, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

7.6 g 4-Aminophenylacetic acid are dissolved in 50 ml 2 N aqueous sodium hydroxide solution and 50 ml acetone. A solution of 8.8 g 4-chlorobenzoyl chloride in 10 ml acetone is added dropwise thereto at 0° C. The reaction mixture is further stirred for 3 hours at ambient temperature, then diluted with water, filtered and the filtrate acidified with dilute hydrochloric acid. The precipitate obtained is reprecipitated via its sodium salt and recrystallized from ethanol. There are obtained 4.2 g (29% of theory) 4-(4-chlorobenzamido)-phenylacetic acid; m.p. 252° C.

Workup

  1. customat 0° C
  2. filtrationfiltered
  3. customThe precipitate obtained
  4. customis reprecipitated via its sodium salt
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-fe180ee47f264eed9baca6fcd913e0f5
Source dataset
uspto-grants-1981_07
Patent number
US04278680

Reaction notes

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