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

HRID 2351331Notes

Reaction equation

HRID 2351331 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-1b11d490d20145d7a0315f486999b212
Source dataset
uspto-grants-1989_10
Patent number
US04873246

Reaction notes

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