Phosphate → HCID 19990443, compound

HRID 346168Notes

Reaction equation

HRID 346168 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].P([O-])([O-])([O-])=O.I[CH3:26]>C(O)C>[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[O:13][CH3:26])=[CH:5][C:4]=1[C:16]([F:19])([F:17])[F:18])#[N:2]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 6328Methyl iodideHCID 199904677-cyano-1-hydroxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione

Product 1

HCID 19990443HCID 19990443, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.3 g (1.1- mmol) 7-cyano-1-hydroxy-6-trifluoromethylquinoxaline 2,3(1H,4H)-dione in 30 ml ethanol was added 15 ml 0.5M phosphate buffer pH 7.4. The mixture was added 1 ml (16 mmol) iodomethane, and then stirred overnight. The reaction mixture was evaporated, and the residue was stirred with water to give a precipitate. Recrystallization (dimethylformamide-water) gave 0.2 g (63%) of 7-cyano-1-methoxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione. M.p. 250° C. decomp. 1H-NMR (DMSO-d6): 7.9 (1H, s), 7.6 (1H, s), 4.07 (3H, s).

Workup

  1. customThe reaction mixture was evaporated
  2. stirringthe residue was stirred with water
  3. customto give a precipitate
  4. customRecrystallization (dimethylformamide-water)

Sources & evidence

ORD record
ord-dc5dbf830101447da9469e0d9feec80d
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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