Water → 1-Benzyloxy-3-chloro-7-cyano-6-trifluoromethylquinoxalin-2(1H)-one

HRID 744006Notes

Reaction equation

HRID 744006 reaction equation
[CH2:1]([O:8][N:9]1[C:18]2[C:13](=[CH:14][C:15]([C:21]([F:24])([F:23])[F:22])=[C:16]([C:19]#[N:20])[CH:17]=2)[NH:12][C:11](=O)[C:10]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)([Cl:29])=O.C1(C)C=CC=CC=1.O>CN(C)C=O>[CH2:1]([O:8][N:9]1[C:18]2[C:13](=[CH:14][C:15]([C:21]([F:24])([F:23])[F:22])=[C:16]([C:19]#[N:20])[CH:17]=2)[N:12]=[C:11]([Cl:29])[C:10]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 6371PhosgeneHCID 194214051-Benzyloxy-7-cyano-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione

Product 1

HCID 194214221-Benzyloxy-3-chloro-7-cyano-6-trifluoromethylquinoxalin-2(1H)-oneYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7.0 g (~19.4 mmol) of 1-benzyloxy-7-cyano-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione in 250 ml of dry N,N-dimethylformamide was added at 0° C. 38.5 ml of 1.93M phosgene in toluene (~74.3 mmol). Stirring was continued at 24° C. for 20 h. The evaporated reaction mixture was stirred with water to give the title compound (6.6 g; 89%).

Workup

  1. customThe evaporated reaction mixture

Sources & evidence

ORD record
ord-4cd758a06bbb4d42bc74c8d1dd349295
Source dataset
uspto-grants-1996_09
Patent number
US05559106

Reaction notes

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