Chloroacetyl chloride → beta-(p-Chloroacetylaminobenzoyl)-propionic acid

HRID 354675

Reaction equation

HRID 354675 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:4][CH:3]=1.[Cl:15][CH2:16][C:17](Cl)=[O:18]>C1(C)C=CC=CC=1>[Cl:15][CH2:16][C:17]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:13][CH:14]=1)=[O:18]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 2432904-(4-Aminophenyl)-4-oxobutanoic acid

Product 1

HCID 20507196beta-(p-Chloroacetylaminobenzoyl)-propionic acidYield 90.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20 g (103 millimoles) of β-(p-aminobenzoyl)-propionic acid and 12.9 g (114 millimoles) of chloroacetyl chloride, together with 200 ml of absolute toluene, are kept for 4 hours at 80° C. The product is filtered off at 10° C., washed with water and dried under reduced pressure at 50° C. 25.1 g (90% of theory) of β-(p-chloroacetylaminobenzoyl)-propionic acid are isolated as light brown crystals which, after recrystallization from acetone, melt at 184°-185° C.

Workup

  1. filtrationThe product is filtered off at 10° C.
  2. washwashed with water
  3. customdried under reduced pressure at 50° C

Sources & evidence

ORD record
ord-da3c5c0beedc4de2ba281a95f4d9df2d
Source dataset
uspto-grants-1983_03
Patent number
US04376771

Linked notes

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