Reaction equation
[CH3:1][C:2]12[CH2:13][CH2:12][CH:5]([C:6](=[N:10][OH:11])[C:7]1=[N:8][NH2:9])[C:4]([CH3:15])([CH3:14])[O:3]2.CO[C:18](OC)(OC)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:19]1([C:18]2[N:9]=[N:8][C:7]3[C:2]4([CH3:1])[CH2:13][CH2:12][CH:5]([C:4]([CH3:15])([CH3:14])[O:3]4)[C:6]=3[N+:10]=2[O-:11])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Participants
3
Procedure
A solution of 2.11 g. (0.01 mole) 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octan-5,6-dione-5-oxime-6-hydrazone in 10 ml. trimethylorthobenzoate is refluxed under nitrogen for 18 hours at a bath temperature of 140° C. during which time all distillate is removed. The resulting mixture is cooled and evaporated to dryness in vacuo. After filtering the residue dissolved in 2% methanol-chloroform through silica gel, and evaporation of the filtrate the resulting solid is triturated with ether, giving 3-phenyl-5,8-dihydro-6,6,8-trimethyl-5,8-ethano-6H-pyrano [4,3-e]-as-triazine-4-oxide; m.p. 186.5° to 189° C.
Workup
- customis removed
- temperatureThe resulting mixture is cooled
- customevaporated to dryness in vacuo
- filtrationAfter filtering the residue
- dissolutiondissolved in 2% methanol-chloroform through silica gel, and evaporation of the filtrate the resulting solid
- customis triturated with ether
Sources & evidence
- ORD record
- ord-849cadca42374098b1c6c433354ce5de
- Source dataset
- uspto-grants-1980_10
- Patent number
- US04228280
Linked notes
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