Dimethylformamide → N-[4-Chloro-3-(trifluoromethyl)phenyl]-N'-(4-hydroxyphenyl)urea

HRID 2094779Notes

Reaction equation

HRID 2094779 reaction equation
CN(C)C=O.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:16])=[O:15])=[CH:9][CH:8]=1.C(N(CC)CC)C.[F:24][C:25]([F:35])([F:34])[C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][C:32]=1[Cl:33])N>C(#N)C>[Cl:33][C:32]1[CH:31]=[CH:30][C:28]([NH:16][C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([OH:6])=[CH:8][CH:9]=2)=[O:15])=[CH:27][C:26]=1[C:25]([F:24])([F:34])[F:35]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 197742N-(4-Hydroxyphenyl)urea

Product 1

HCID 25221150N-[4-Chloro-3-(trifluoromethyl)phenyl]-N'-(4-hydroxyphenyl)ureaYield 76.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To the dry N,N-dimethylformamide (45 ml) and 1-(4-hydroxyphenyl)urea (15 g, 0.0985 mol) solution were added triethylamine (34 ml, 0.24646 mol) and 3-trifluoromethyl-4-chloroaniline (19.28 g, 0.0985 mol) in one lot. This reaction mass was then agitated at 100° C. for 10-12 hours, quenched in water and the aqueous layer was extracted with ethyl acetate. The ethyl acetate layer was back washed with water and dried over sodium sulfate. It was evaporated under vacuum to obtain solid. The obtained solid was slurried in acetonitrile (100 ml) at ambient temperature, filtered and washed repeatedly with acetonitrile till the clear filtrate was obtained. The obtained cake was then suck dried for 10 minutes and vacuum dried at 50° C. to give 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(4-hydroxyphenyl)urea (25 g).

Workup

  1. customquenched in water
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe ethyl acetate layer was back washed with water
  4. dry with materialdried over sodium sulfate
  5. customIt was evaporated under vacuum
  6. customto obtain solid
  7. filtrationfiltered
  8. washwashed repeatedly with acetonitrile till the clear filtrate
  9. customwas obtained
  10. customThe obtained cake was then suck dried for 10 minutes
  11. customvacuum dried at 50° C.

Sources & evidence

ORD record
ord-26b1e6f9c4db4642ab4f253beff80198
Source dataset
uspto-grants-2013_05
Patent number
US08445687B2

Reaction notes

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