Triethyl orthoacetate → 2-(3-Iodo-4-methylphenyl)-5-methyl-1,3,4-oxadiazole

HRID 1619145

Reaction equation

HRID 1619145 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([NH:7][NH2:8])=[O:6].[C:13](OCC)(OCC)(OCC)[CH3:14]>C(O)(=O)C>[I:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][C:13]([CH3:14])=[N:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 66221Triethyl orthoacetateHCID 597325003-Iodo-4-methylbenzohydrazide

Product 1

HCID 581704972-(3-Iodo-4-methylphenyl)-5-methyl-1,3,4-oxadiazoleYield 78.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

A stirred mixture of 3-iodo-4-methylbenzohydrazide (preparation 55b, 5.00 g, 18.1 mmol) and triethyl orthoacetate (11.00 mL, 58.2 mmol) in acetic acid (30 mL) were heated to 150° C. in a sealed tube. After 3 hours, the mixture was cooled and concentrated in vacuo. Aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with dichloromethane. The organic solution was dried (MgSO4) and the solvent was removed in vacuo. The crude material was purified by flash chromatography (2:1 hexanes/ethyl acetate) to give the title compound (4.26 g, 78%) as a white solid.

Workup

  1. temperaturethe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. additionAqueous sodium hydrogen carbonate solution was added
  4. extractionthe mixture was extracted with dichloromethane
  5. dry with materialThe organic solution was dried (MgSO4)
  6. customthe solvent was removed in vacuo
  7. customThe crude material was purified by flash chromatography (2:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-a59ed7b6760e45f59b06d99d623f4516
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Linked notes

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