Benzyl Bromide → 1-Benzyloxy-7-cyano-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione

HRID 744005Notes

Reaction equation

HRID 744005 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([NH:7][C:8](=[O:15])[C:9](=[O:14])[N:10]2[OH:13])=[CH:5][C:4]=1[C:16]([F:19])([F:18])[F:17])#[N:2].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C.P([O-])(O)(O)=O.[K+]>[CH2:20]([O:13][N:10]1[C:11]2[C:6](=[CH:5][C:4]([C:16]([F:19])([F:17])[F:18])=[C:3]([C:1]#[N:2])[CH:12]=2)[NH:7][C:8](=[O:15])[C:9]1=[O:14])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 199904677-cyano-1-hydroxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione

Product 1

HCID 194214051-Benzyloxy-7-cyano-6-trifluoromethylquinoxaline-2,3(1H,4H)-dioneYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516951Monobasic potassium phosphateSolvent

Procedure

To a solution of 10.0 g (~36.9 mmol) of 7-cyano-1-hydroxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione in a mixture of 700 ml of ethanol and 175 ml of 1M potassium dihydrogen phosphate buffer pH 7.4 was added 14 g (~81 mmol) of benzylbromide. Stirring was continued for 2 h at 25° C. The precipitate was filtered off and washed with ice-cold ethanol to give the title compound (9.9 g; 75%).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with ice-cold ethanol

Sources & evidence

ORD record
ord-b90f781ab93444328cb8bf81827d8e1d
Source dataset
uspto-grants-1996_09
Patent number
US05559106

Reaction notes

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