Water → HCID 735611, compound

HRID 432876Notes

Reaction equation

HRID 432876 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:15]1([N:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22](Cl)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C(OCC)(=O)C>[C:15]1([N:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=2)=[O:23])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 97314-FluoroanilineHCID 65741N,N-Diphenylcarbamic chloride

Product 1

HCID 735611HCID 735611, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-fluoroaniline (0.2 g) in dichlbromethane (10 ml) were added in turn pyridine (0.19 ml) and diphenylcarbamoyl chloride (0.417 g) at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 10 hours, and to the mixture was added N,N-dimethylaminopyridine (0.22 g), and the mixture was allowed to stir for another 1 hour. The reaction mixture 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 N,N-diphenyl-N′-4-fluorophenylurea (0.384 g).

Workup

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

Sources & evidence

ORD record
ord-851d4463f7a644f49b773ca34976ef99
Source dataset
uspto-grants-2003_12
Patent number
US06664293B2

Reaction notes

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