Dimethylformamide → N'-cyclopropyl-N-(2,5-difluorophenyl)-N-formylurea

HRID 1446777Notes

Reaction equation

HRID 1446777 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][CH:10]=[O:11].CN(C)C=O.[CH:17]1([N:20]=[C:21]=[O:22])[CH2:19][CH2:18]1.C(N(CC)CC)C>CCOCC.O>[CH:17]1([NH:20][C:21](=[O:22])[N:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])[CH:10]=[O:11])[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 637659IsocyanatocyclopropaneHCID 12803461N-(2,5-difluorophenyl)formamide

Product 1

HCID 12803462N'-cyclopropyl-N-(2,5-difluorophenyl)-N-formylurea

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 9.9 g of 2B, 25 ml of dimethylformamide, 11 g of 1A and 2 g of triethylamine (catalyst) was heated in a steam bath for 24 hours. The resulting mixture was diluted with ether and water, and phase-separated. The ether phase was washed with water, and dried (MgSO4), and the solvent was evaporated. The residue was triturated with ether. The residual off-white solid was 2, m.p.: 118°-120° C.

Workup

  1. temperaturewas heated in a steam bath for 24 hours
  2. customphase-separated
  3. washThe ether phase was washed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated
  6. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-5afd850b23af4ca2a9346e2612c96860
Source dataset
uspto-grants-1982_02
Patent number
US04313755

Reaction notes

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