Trimethyl orthobeznoate → HCID 12767938, compound

HRID 895002Notes

Reaction equation

HRID 895002 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])[CH:4]([CH3:14])[O:3]2.CO[C:17](OC)(OC)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:18]1([C:17]2[N:9]=[N:8][C:7]3[C:2]4([CH3:1])[CH2:13][CH2:12][CH:5]([CH:4]([CH3:14])[O:3]4)[C:6]=3[N+:10]=2[O-:11])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 69720Trimethyl orthobeznoateHCID 136359185HCID 136359185, compound

Product 1

HCID 12767938HCID 12767938, compound

Procedure

A solution of 1.97 g. (0.01 mole) 1,3-dimethyl-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 gives 3-phenyl-5,8-dihydro-6,8-dimethyl-5,8-ethano-6H-pyrano[4,3-e]-as-triazine-4-oxide.

Workup

  1. customis removed
  2. temperatureThe resulting mixture is cooled
  3. customevaporated to dryness in vacuo
  4. filtrationAfter filtering the residue
  5. dissolutiondissolved in 2% methanol-chloroform through silica gel, and evaporation of the filtrate

Sources & evidence

ORD record
ord-7d43c29ca1bb4130a88319a0e41efa42
Source dataset
uspto-grants-1981_08
Patent number
US04285944

Reaction notes

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