Phenol → HCID 67717948, compound

HRID 1290648Notes

Reaction equation

HRID 1290648 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:11]1[O:12][C:13]2[C:19]([N:20]3[C:25](=[O:26])[CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[N:22]([CH3:31])[C:21]3=[O:32])=[C:18]([F:33])[CH:17]=[C:16]([Cl:34])[C:14]=2[N:15]=1>CN(C)C=O>[Cl:34][C:16]1[C:14]2[N:15]=[C:11]([O:9][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[O:12][C:13]=2[C:19]([N:20]2[C:25](=[O:26])[CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[N:22]([CH3:31])[C:21]2=[O:32])=[C:18]([F:33])[CH:17]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 18916426HCID 18916426, compound

Product 1

HCID 67717948HCID 67717948, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Under a nitrogen atmosphere, a stirred solution of 2.0 grams (51 mmole) of 60% sodium hydride (in mineral oil) in 25 mL of N,N-dimethylformamide is cooled in an ice bath, and a solution of 5.3 grams (56.3 mmoles) of phenol in 25 mL of N,N-dimethylformamide is added dropwise during a five minute period. To this is added a solution of 20.3 grams (51 mmole) of 3-(2,4-dichloro-6-fluorobenzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)pyrimidinedione (as prepared in Example 24) in 25 mL of N,N-dimethylformamide. Upon completion of the addition the reaction mixture is allowed to warm to ambient temperature, where it stirs for about 18 hours. After this time the reaction mixture is concentrated under reduced pressure, yielding 3-(4-chloro-6-fluoro-2-phenoxybenzoxazol-7-yl]-1-methyl-6-trifluoromethyl-2,4-(1H,3H)pyrimidinedione.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. concentrationAfter this time the reaction mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-c0f05910901b4f84adf0bc31fa72c34c
Source dataset
uspto-grants-1998_05
Patent number
US05753595

Reaction notes

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