Acetone Cyanohydrin → HCID 56968103, compound

HRID 1852897Notes

Reaction equation

HRID 1852897 reaction equation
[CH3:1][C:2]1([CH3:24])[C:11]2[C:6](=[N:7][CH:8]=[CH:9][N:10]=2)/[C:5](=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])/[O:4][C:3]1=[O:23].C(N(CC)CC)C.CC(C)(O)C#N>C(#N)C>[CH3:1][C:2]1([CH3:24])[C:11]2[N:10]=[CH:9][CH:8]=[N:7][C:6]=2[C:5](=[O:4])[CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:20])([F:21])[F:22])[C:3]1=[O:23]

Participants

5

Reactant 3

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 69082945HCID 69082945, compound

Product 1

HCID 56968103HCID 56968103, compoundYield 111.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 8,8-dimethyl-5-[1-(2-trifluoromethyl-phenyl)-meth-(Z)-ylidene]-5,8-dihydro-pyrano[3,4-b]pyrazin-7-one (0.170 g) in acetonitrile (1.7 ml) at ambient temperature was added triethylamine (0.154 g) and 4□ molecular sieves. After 10 min acetone cyanohydrin (0.013 g) was added and the reaction mixture stirred for 16 hours. The reaction mixture was concentrated and the residue purified by chromatography on silica gel (eluent 5-95% ethyl acetate in isohexane) to give the crude 8,8-dimethyl-6-(2-trifluoromethyl-phenyl)-8H-quinoxaline-5,7-dione (compound E1 of Table E) (0.190 g) which was carried over to the next step.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by chromatography on silica gel (eluent 5-95% ethyl acetate in isohexane)

Sources & evidence

ORD record
ord-240a140fc3fb45d58977fd76783df54b
Source dataset
uspto-grants-2015_02
Patent number
US08962628B2

Reaction notes

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