Cyclohexyl bromide → HCID 19990417, compound

HRID 346169Notes

Reaction equation

HRID 346169 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.[CH:27]1(Br)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>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][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:5][C:4]=1[C:16]([F:19])([F:17])[F:18])#[N:2]

Participants

5

Reactant 3

HCID 7960Cyclohexyl bromideHCID 8471TriethylamineHCID 199904677-cyano-1-hydroxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione

Product 1

HCID 19990417HCID 19990417, compound

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 0.7 ml triethylamine and 1.5 ml (12 mmol) cyclohexylbromide. The reaction mixture was refluxed for 7 days and then evaporated in vacuo. The residue was stirred with water to give a precipitate (0.25 g. Recrystallization (dimethylformamide-water) gave 0.17 g (44%) of 7-cyano-1-cyclohexyloxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione). M.p. 259° C. decomp. 1H-NMR (DMSO-d6): 8.0 (1H, s), 7.6 (1H, s), 4.3 (1H, m), 1.4 (8H, m).

Workup

  1. temperatureThe reaction mixture was refluxed for 7 days
  2. customevaporated in vacuo
  3. customto give
  4. customa precipitate (0.25 g. Recrystallization (dimethylformamide-water) gave 0.17 g (44%) of 7-cyano-1-cyclohexyloxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione)

Sources & evidence

ORD record
ord-e6d29003c44d4356a642122cf4c5fa97
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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