Water → 1-allyloxy-7-cyano-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione

HRID 346167Notes

Reaction equation

HRID 346167 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.[CH2:25](Br)[CH:26]=[CH2:27].O>C(O)C>[CH2:27]([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])[CH:26]=[CH2:25]

Participants

6

Reactant 4

HCID 962WaterHCID 1061PhosphateHCID 7841Allyl bromideHCID 199904677-cyano-1-hydroxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione

Product 1

HCID 199904481-allyloxy-7-cyano-6-trifluoromethylquinoxaline-2,3(1H,4H)-dioneYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 0.4 g (1.5 mmol) 7-cyano-1-hydroxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione in 40 ml ethanol was added 20 ml 0.5 M phosphate buffer pH 7.4. The mixture was added 0.8 ml (9.3 mmol) allyl bromide, and then stirred at 25° C. for 4 h. Addition of 80 ml water gave 0.33 g (72%) 1-allyloxy-7-cyano-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione as a precipitate. M.p. 239° C. decomp. (methanol-water). NMR (DMSO-d6) 7.9 (1H, s), 7.6 (1H, s), 6.1 (1H, m), 5.4 (2H, m), 4.7 (2H, d).

Sources & evidence

ORD record
ord-531c3a9cc1ee40c6a91d51eb95d981de
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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