Triethylamine → 7-cyano-1-phenoxycarbonyloxy-6-trifluoromethylquinoxaline-2,3-(1H,4H)-dione

HRID 346140Notes

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].C(N(CC)CC)C.Cl[C:28]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29]>O1CCCC1>[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][C:28]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:29])=[CH:5][C:4]=1[C:16]([F:19])([F:17])[F:18])#[N:2]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 0.4 g (1.48 mmol) 7-cyano-1-hydroxy-6-trifluoromethylquinoxaline -2,3(1H,4H)-dione in 50 ml dry tetrahydrofuran was added 0.225 ml (1.63 mmol) dry triethylamine and 0.2 ml (1.58 mmol) phenyl chloroformate. The mixture was stirred at 25° C. for 30 min., and then filtered and evaporated in vacuo. The residue was stirred with ether to give 0.48 g (83%) of 7-cyano-1-phenoxycarbonyloxy-6-trifluoromethylquinoxaline-2,3-(1H,4H)-dione. M.p. 190° C. decomp. 1H-NMR (DMSO-d6): 8.43 (1H,s), 7.63 (1H, s), 7.3 (5H, broad s).

Workup

filtrationfiltered
customevaporated in vacuo
stirringThe residue was stirred with ether

Sources & evidence

ORD record: ord-fb0a15971e8e430dad4603c3a94073fb
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05061706

Reaction notes

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