Water → (4-fluorobenzoylamino)-diphenylmethane

HRID 432875Notes

Reaction equation

HRID 432875 reaction equation
[NH2:1][CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CC=CC=1.[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1.O>ClCCl.C(OCC)(=O)C>[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:1][CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:27])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7036BenzhydrylamineHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 867469(4-fluorobenzoylamino)-diphenylmethane

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of aminodiphenylmethane (0.4 g) in dichloromethane (5 ml) were added in turn pyridine (0.21 ml) and 4-fluorobenzoyl chloride (0.23 ml) at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 1 hour, which was taken up into a mixture of water and ethyl acetate. The separated organic layer was washed in turn with hydrochloric acid (1N), aqueous sodium hydrogen carbonate and brine, and dried over magnesium sulfate. Evaporation under reduced pressure gave a residue, which was triturated with diisopropyl ether to give (4-fluorobenzoylamino)-diphenylmethane (0.49 g).

Workup

  1. washThe separated organic layer was washed in turn with hydrochloric acid (1N), aqueous sodium hydrogen carbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation under reduced pressure
  4. customgave a residue, which
  5. customwas triturated with diisopropyl ether

Sources & evidence

ORD record
ord-f393bc14bf954c79823d8a2b5aab4071
Source dataset
uspto-grants-2003_12
Patent number
US06664293B2

Reaction notes

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