Water → (4-fluorobenzoylamino)-diphenylmethane

HRID 1295389Notes

Reaction equation

HRID 1295389 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-5406e5652fda40439209dcc53f957880
Source dataset
uspto-grants-2007_07
Patent number
US07241811B2

Reaction notes

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