Hydrochloric Acid → HCID 12084697, compound

HRID 497057Notes

Reaction equation

HRID 497057 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1.CN(C1C=CC=CN=1)C.Cl>C(Cl)(Cl)Cl.C(OCC)(=O)C.O.CN(C=O)C>[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([N:14]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:27])=[CH:24][CH:23]=1

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 218852-DimethylaminopyridineHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 12084697HCID 12084697, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate and ethyl bromoacetate were added to DMF solution of aniline and stirred under heating. After adding water and ethyl acetate to the reaction mixture, the organic layer was separated, washed and dried, and then the solvent was evaporated under a reduced pressure to obtain a crude product. This was dissolved in chloroform, mixed with TEA, 4-fluorobenzoyl chloride and dimethylaminopyridine (DMAP) and stirred. After adding 1 M hydrochloric acid to the reaction solution, the organic layer was separated, washed and dried, and then the solvent was evaporated under a reduced pressure. By purifying the thus obtained crude product by a silica gel column chromatography (to be referred to as SCG hereinafter), ethyl [(4-fluorobenzoyl)phenylamino]acetate (colorless oil) was obtained.

Workup

  1. temperatureunder heating
  2. customthe organic layer was separated
  3. washwashed
  4. customdried
  5. customthe solvent was evaporated under a reduced pressure
  6. customto obtain a crude product
  7. stirringstirred
  8. customthe organic layer was separated
  9. washwashed
  10. customdried
  11. customthe solvent was evaporated under a reduced pressure
  12. customBy purifying the
  13. customthus obtained crude product by a silica gel column chromatography (to be referred to as SCG hereinafter)

Sources & evidence

ORD record
ord-181ff357eb384a06bcd4c17b056e1af4
Source dataset
uspto-grants-2005_09
Patent number
US06949543B2

Reaction notes

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