Water → 3-(4-Chloro-6-fluoro-3-methyl-2-phenoxycarbonylaminophenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

HRID 1265383Notes

Reaction equation

HRID 1265383 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([N:22]=[C:23]=[O:24])[C:3]=1[CH3:25].C(N(CC)CC)C.[C:33]1([OH:39])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([NH:22][C:23]([O:39][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:24])[C:3]=1[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 8471TriethylamineHCID 865859043-(4-Chloro-6-fluoro-2-isocyanato-3-methylphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Product 1

HCID 572893993-(4-Chloro-6-fluoro-3-methyl-2-phenoxycarbonylaminophenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedioneYield 45.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-(4-Chloro-6-fluoro-2-isocyanato-3-methylphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (1.4 mmol) and triethylamine (0.14 g, 1.4 mmol) were dissolved in toluene (15 ml) and the solution was treated with phenol (0.13 g, 1.4 mmol). Solution was stirred for 0.3 hr at ambient temperature and water was added. Product was extracted with ethyl acetate. Removal of the solvent followed by column chromatography on silica gel (eluent, methylene chloride) afforded the title compound (0.3 g).

Workup

  1. extractionProduct was extracted with ethyl acetate
  2. customRemoval of the solvent

Sources & evidence

ORD record
ord-e51e7dc38b8b48ddb69c53fcfb4fdbfc
Source dataset
uspto-grants-2003_04
Patent number
US06545161B2

Reaction notes

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