Triethyl orthoacetate → HCID 44478380, compound

HRID 452830Notes

Reaction equation

HRID 452830 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3=[N:14][C:15]([C:18]([NH:20][NH2:21])=[O:19])=[CH:16][CH:17]=[C:12]3[O:11][CH:10]=2)=[CH:5][CH:4]=1.[C:22](OCC)(OCC)(OCC)[CH3:23].N12CCCN=C1CCCCC2>C(O)CCC>[CH3:22][C:23]1[O:19][C:18]([C:15]2[N:14]=[C:13]3[C:9]([C:6]4[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=4)=[CH:10][O:11][C:12]3=[CH:17][CH:16]=2)=[N:20][N:21]=1

Participants

5

Reactant 3

HCID 66221Triethyl orthoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 44481480HCID 44481480, compound

Product 1

HCID 44478380HCID 44478380, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 3-[4-(methylthio)phenyl]furo[3,2-b]pyridine-5-carbohydrazide (0.20 g, 0.68 mmol) and triethyl orthoacetate (0.27 mL, 1.49 mmol) in n-butanol (5 mL) was heated under reflux for 1.5 hr. 1,8-Diazabicyclo[5.4.0]undec-7-ene (0.10 mL, 0.68 mmol) was added to the reaction mixture, and the mixture was further heated under reflux overnight. After cooling, the precipitate was collected by filtration and recrystallized from hexane/ethyl acetate to give the title compound (0.15 g, yield 67%) as colorless crystals.

Workup

  1. temperatureunder reflux for 1.5 hr
  2. temperaturethe mixture was further heated
  3. temperatureunder reflux overnight
  4. temperatureAfter cooling
  5. filtrationthe precipitate was collected by filtration
  6. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-ef78ff2bae2a4eaba74ac97e64ab7eb1
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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