Trimethyl orthobeznoate → HCID 20323691, compound

HRID 839581Notes

Reaction equation

HRID 839581 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([NH:8][NH2:9])=[O:7].CO[C:12](OC)(OC)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[C:13]1([C:12]2[N:1]3[CH:5]=[CH:4][N:3]=[C:2]3[C:6](=[O:7])[NH:8][N:9]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 69720Trimethyl orthobeznoateHCID 12493320HCID 12493320, compound

Product 1

HCID 20323691HCID 20323691, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2.6 gm. portion of 2-imidazolecarboxylic acid hydrazide is added to 200 ml. of ethanol. To this is added 20 ml. of trimethylorthobenzoate. The mixture is refluxed for 31 hours, then the solvents are evaporated giving a white solid which is washed twice with diethyl ether giving 3.0 gm. of white solid. This solid is combined with 50 ml. of diphenyl ether and heated with stirring in an oil bath at 265°-275° C. for 10 minutes. The mixture is cooled, petroleum ether is added and the mixture is filtered. The solid is washed twice with hot petroleum ether, giving 1.4 gm. of the desired product as a light tan solid, m.p. 292°-295° C.

Workup

  1. additionTo this is added 20 ml
  2. temperatureThe mixture is refluxed for 31 hours
  3. customthe solvents are evaporated
  4. customgiving a white solid which
  5. washis washed twice with diethyl ether giving 3.0 gm
  6. temperatureof diphenyl ether and heated
  7. temperatureThe mixture is cooled
  8. additionpetroleum ether is added
  9. filtrationthe mixture is filtered
  10. washThe solid is washed twice with hot petroleum ether
  11. customgiving 1.4 gm

Sources & evidence

ORD record
ord-f8ec96467a4c423aad6f340a91e45337
Source dataset
uspto-grants-1978_06
Patent number
US04096257

Reaction notes

Loading…