4-Chlorobutyryl chloride → 4-chloro-N,N-bis(4-fluorophenyl)butanamide

HRID 1073175Notes

Reaction equation

HRID 1073175 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[Cl:16][CH2:17][CH2:18][CH2:19][C:20](Cl)=[O:21]>CC1C=CC=CC=1>[Cl:16][CH2:17][CH2:18][CH2:19][C:20]([N:8]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:21]

Participants

4

Reactant 2

HCID 783704-Chlorobutyryl chlorideHCID 112411734-Fluoro-N-(4-fluorophenyl)benzenamine

Product 1

HCID 150877884-chloro-N,N-bis(4-fluorophenyl)butanamideYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 35 parts of 4-fluoro-N-(4-fluorophenyl)benzenamine, 107 parts of 4-chlorobutanoyl chloride and 130 parts of methylbenzene was stirred for 2 hours at reflux temperature. The reaction mixture was washed with a sodium chloride solution, dried, filtered and evaporated. The residue was distilled to remove the excess of 4-chlorobutanoyl chloride, yielding 47 parts (95.0%) of 4-chloro-N,N-bis(4-fluorophenyl)butanamide as a residue (int. 69).

Workup

  1. temperatureat reflux temperature
  2. washThe reaction mixture was washed with a sodium chloride solution
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. distillationThe residue was distilled
  7. customto remove the excess of 4-chlorobutanoyl chloride

Sources & evidence

ORD record
ord-c96c33ad82134a3da284d51f5007bdcb
Source dataset
uspto-grants-1990_11
Patent number
US04968684

Reaction notes

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