Acetone → 3-chloro-N-phenylpropanamide

HRID 620008Notes

Reaction equation

HRID 620008 reaction equation
[Cl:1][CH2:2][CH2:3][C:4](Cl)=[O:5].CC(C)=O.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>O>[Cl:1][CH2:2][CH2:3][C:4]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5]

Participants

6

Reactant 4

HCID 180Acetone2×HCID 313Hydrochloric AcidHCID 6115AnilineHCID 693643-Chloropropionyl chloride

Product 1

HCID 2404043-chloro-N-phenylpropanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-chloropropionyl chloride (300 ml) and acetone (600 ml) is added dropwise to a refluxing mixture of aniline (575 ml) and acetone (600 ml). The reaction mixture is refluxed for one hour, cooled in an ice bath, and poured into a mixture of 6N HCl (500 ml) and water (3.5 l). The resulting solid is filtered, washed with water, and dried, yielding the desired product, M.P. 114°-115.5° C.

Workup

  1. temperatureThe reaction mixture is refluxed for one hour
  2. temperaturecooled in an ice bath
  3. filtrationThe resulting solid is filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6d3202c895954af697ce840462fbfe2a
Source dataset
uspto-grants-1989_04
Patent number
US04818755

Reaction notes

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