N-(4-Benzyloxy-2-fluorophenyl)-N'-(4-fluorophenyl)-N-methylurea → N-(2-fluoro-4-hydroxyphenyl)-N'-(4-fluorophenyl)-N-methylurea

HRID 1010411Notes

Reaction equation

HRID 1010411 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH3:26])[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[O:17])=[C:11]([F:27])[CH:10]=1)C1C=CC=CC=1>CO.[C].[Pd]>[F:27][C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][C:12]=1[N:15]([CH3:26])[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[O:17]

Participants

4

Reactant 1

HCID 22936494N-(4-Benzyloxy-2-fluorophenyl)-N'-(4-fluorophenyl)-N-methylurea

Product 1

HCID 22936763N-(2-fluoro-4-hydroxyphenyl)-N'-(4-fluorophenyl)-N-methylureaYield 71.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

After dissolving N-(4-benzyloxy-2-fluorophenyl)-N′-(4-fluorophenyl)-N-methylurea (105 mg, 0.2881 mmol) in methanol (10 ml), 10% palladium carbon (20 mg) was added and the mixture was stirred for 45 minutes at room temperature under a hydrogen atmosphere. The catalyst was filtered off, and then was washed with ethanol, and the solvent of the filtrate was distilled off under reduced pressure. The precipitated crystals were suspended in diethyl ether, and then filtered out, washed with diethyl ether and dried by aspiration to obtain the title compound (57 mg, 0.2048 mmol, 71.10%) as colorless crystals.

Workup

  1. additionwas added
  2. filtrationThe catalyst was filtered off
  3. washwas washed with ethanol
  4. distillationthe solvent of the filtrate was distilled off under reduced pressure
  5. filtrationfiltered out
  6. washwashed with diethyl ether
  7. customdried by aspiration

Sources & evidence

ORD record
ord-dd9ce577c27542e18abb89060c8d89e0
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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