1,1,1-Trimethoxybutane → HCID 20323690, compound

HRID 839580Notes

Reaction equation

HRID 839580 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)[CH2:13][CH2:14][CH3:15]>C(O)C>[CH2:13]([C:12]1[N:1]2[CH:5]=[CH:4][N:3]=[C:2]2[C:6](=[O:7])[NH:8][N:9]=1)[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 12493320HCID 12493320, compound

Product 1

HCID 20323690HCID 20323690, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 37.0 gm. of 2-imidazolecarboxylic acid hydrazide, prepared by the method of U.S. Pat. No. 3,600,399, 2.5 liters of ethanol and 325 ml. of trimethylorthobutyrate is refluxed overnight and evaporated to a solid. This solid is ground, added to 400 ml. of diphenyl ether and heated in an oil bath at 220°-245° C. for 30 minutes. The mixture is cooled to room temperature and crystallized by the addition of 100 ml. of petroleum ether. The solid is collected, washed twice with petroleum ether, recrystallized from 300 ml. of a hot mixture of ethanol and methanol and treated with charcoal giving 53.5 gm. of the desired final product, m.p. 153°-159° C.

Workup

  1. additionA mixture of 37.0 gm
  2. customevaporated to a solid
  3. additionadded to 400 ml
  4. temperatureof diphenyl ether and heated in an oil bath at 220°-245° C. for 30 minutes
  5. customcrystallized by the addition of 100 ml
  6. customThe solid is collected
  7. washwashed twice with petroleum ether
  8. customrecrystallized from 300 ml
  9. additionof a hot mixture of ethanol and methanol
  10. additiontreated with charcoal giving 53.5 gm

Sources & evidence

ORD record
ord-f2f3836aa9174430b6c7906139cb523b
Source dataset
uspto-grants-1978_06
Patent number
US04096257

Reaction notes

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