Chloroacetyl chloride → HCID 14230257, compound

HRID 35298Notes

Reaction equation

HRID 35298 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[NH2:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:23][CH2:24][C:25](Cl)=[O:26]>CC(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[NH:9][C:25](=[O:26])[CH2:24][Cl:23])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 109550394-Fluoro-alpha-(4-fluorophenyl)benzenemethanamine

Product 1

HCID 14230257HCID 14230257, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 21.9 parts of 4-fluoro-α-(4-fluorophenyl)benzenemethanamine in 160 parts of 2-propanone were added 11.66 parts of sodium carbonate. Then there were added dropwise 12.43 parts of 2-chloroacetyl chloride at a temperature below 30° C. (cooling in an ice-bath was necessary). Upon completion, stirring was continued first for one hour at room temperature and further for 2 hours at reflux. After cooling to room temperature, the sodium carbonate was filtered off and washed with 2-propanone. The filtrate was evaporated and the residue was crystallized from 2,2'-oxybispropane, yielding 20.6 parts of N-[bis(4-fluorophenyl)-methyl]-2-chloroacetamide; mp. 127.6° C. (intermediate 4).

Workup

  1. temperatureat a temperature below 30° C. (cooling in an ice-bath was necessary)
  2. temperatureat reflux
  3. filtrationthe sodium carbonate was filtered off
  4. washwashed with 2-propanone
  5. customThe filtrate was evaporated
  6. customthe residue was crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-a408251db1914c48b3027932cbc81580
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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