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

HRID 1619145

반응식

HRID 1619145 반응식
[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]

참가 물질

4

반응물 2

HCID 66221Triethyl orthoacetateHCID 597325003-Iodo-4-methylbenzohydrazide

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
150 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a59ed7b6760e45f59b06d99d623f4516
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772288B2

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