3-Chloropropionyl chloride → 3-[p-(3-Chloropropionylamino)-benzoyl]-propionic acid

HRID 1110327Notes

Reaction equation

HRID 1110327 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][CH2:17][C:18](Cl)=[O:19]>CC(C)=O>[Cl:15][CH2:16][CH2:17][C:18]([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:19]

Participants

4

Reactant 2

HCID 693643-Chloropropionyl chlorideHCID 2432904-(4-Aminophenyl)-4-oxobutanoic acid

Product 1

HCID 221549983-[p-(3-Chloropropionylamino)-benzoyl]-propionic acidYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

19.2 g (100 millimoles) of 3-(p-aminobenzoyl)-propionic acid were stirred with 24.8 g (195 millimoles) of 3-chloropropionyl chloride in 200 ml of absolute acetone for 10 hours at room temperature. The mixture was then evaporated down, the residue was stirred with 200 ml of water, and the product was filtered off under suction at 10° C., washed with cold acetone and dried at 100° C. under reduced pressure. 21 g (75%) of 3-[p-(3-chloropropionylamino)-benzoyl]-propionic acid were obtained as yellowish crystals of melting point 181°-182° C. (acetonitrile).

Workup

  1. customThe mixture was then evaporated down
  2. filtrationthe product was filtered off under suction at 10° C.
  3. washwashed with cold acetone
  4. customdried at 100° C. under reduced pressure

Sources & evidence

ORD record
ord-760c05f35e78473d8d40d34b0ef32d30
Source dataset
uspto-grants-1990_12
Patent number
USRE033476

Reaction notes

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