2,6-Difluorobenzoyl isocyanate → N-[3,5-Dichloro-2-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-N'-(2,6-difluorobenzoyl)-N-ethylurea

HRID 1419628Notes

Reaction equation

HRID 1419628 reaction equation
[Cl:1][C:2]1[C:3]([F:22])=[C:4]([CH:8]=[C:9]([Cl:21])[C:10]=1[O:11][C:12]([F:20])([F:19])[CH:13]([F:18])[C:14]([F:17])([F:16])[F:15])[NH:5][CH2:6][CH3:7].[F:23][C:24]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:25]=1[C:26]([N:28]=[C:29]=[O:30])=[O:27].CCCCCCC.C(OCC)(=O)C>ClCCCl.ClC(Cl)C>[Cl:1][C:2]1[C:3]([F:22])=[C:4]([N:5]([CH2:6][CH3:7])[C:29]([NH:28][C:26](=[O:27])[C:25]2[C:31]([F:35])=[CH:32][CH:33]=[CH:34][C:24]=2[F:23])=[O:30])[CH:8]=[C:9]([Cl:21])[C:10]=1[O:11][C:12]([F:19])([F:20])[CH:13]([F:18])[C:14]([F:17])([F:16])[F:15]

Participants

6

Reactant 3

HCID 27333692,6-Difluorobenzoyl isocyanate2×HCID 155103103,5-dichloro-2-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)-N-ethyl anilineHCID 21899848Ethylacetate heptane

Product 1

HCID 9850704N-[3,5-Dichloro-2-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-N'-(2,6-difluorobenzoyl)-N-ethylureaYield 110.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1.00 g 3,5-dichloro-2-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)-N-ethyl aniline in 2 mL 1,2-dichloroethane under an atmosphere of nitrogen at room temperature there was added 0.54 g 2,6-difluorobenzoyl isocyanate dissolved in 6 mL dichloroethane dropwise over a 10 minute period. The mixture was stirred and warmed to 40° C. for a 1.5 hour period. Analysis by thin layer chromatography silica gel 4:1 heptane/ethyl acetate indicated incomplete reaction. To the mixture was added 0.13 g 2,6-difluorobenzoyl isocyanate in 1.5 mL 1,2-dichloroethane, and the mixture was warmed at 40° C. for 2.5 hour. Analysis by TLC indicated complete reaction. The reaction mixture was concentrated under vacuum to give an oil 1.64 g, which was chromatographed using a Michel-Miller low pressure silica gel column eluted with 4:1 heptane/ethyl acetate. Like fractions were pooled and concentrated under vacuum to give a white solid 0.87 g, mp 106°-14° C. Proton nmr and mass spectra were consistent with the proposed structure. Anal. calcd C19H11Cl2F9N2O3 : C, 40.95; H, 1.99; N, 5.03. Found: C, 40.89; H, 1.92; N, 5.03.

Workup

  1. temperaturethe mixture was warmed at 40° C. for 2.5 hour
  2. customreaction
  3. concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-a04932b7cfcd44b7b1e84c066d2c5b94
Source dataset
uspto-grants-1999_03
Patent number
US05886221

Reaction notes

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