Toluene → 1-Benzyloxy-3-chloro-7-trifluoromethylquinoxalin-2(1H)-one

HRID 744011Notes

Reaction equation

HRID 744011 reaction equation
[C:1]([Cl:4])(Cl)=O.[C:5]1([CH3:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C([N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:29]([F:32])([F:31])[F:30])[CH:27]=2)[NH:22]C(=O)[C:20]1=[O:34])C1C=CC=CC=1.CN(C)C=[O:38]>>[CH2:11]([O:38][N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:29]([F:32])([F:31])[F:30])[CH:27]=2)[N:22]=[C:1]([Cl:4])[C:20]1=[O:34])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 6371PhosgeneHCID 194214551-benzyl-7-trifluoromethylquinoxaline-2,3(1H,4H)-dione

Product 1

HCID 194214471-Benzyloxy-3-chloro-7-trifluoromethylquinoxalin-2(1H)-oneYield 96%

Conditions

Temperature
0 °C

Procedure

A solution of 20% phosgene in toluene (120 ml, 0.23 mol) was added to a solution of 1-benzyl-7-trifluoromethylquinoxaline-2,3(1H,4H)-dione (27 g, 80 mmol) in 300 ml of dry N,N-dimethylformamide with stirring at 0° C. The mixture was stirred at room temperature overnight and evaporated to dryness. The residue was triturated with ice/water, filtered and dried in vacuo over phosphorus pentoxide to give 27.4 g (96%) of the title compound. M.p. 148°-150° C.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customevaporated to dryness
  3. customThe residue was triturated with ice/water
  4. filtrationfiltered
  5. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-90aedd0b1fe14d25b1ff5cd33599522a
Source dataset
uspto-grants-1996_09
Patent number
US05559106

Reaction notes

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