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

HRID 1619145

反応式

HRID 1619145 の反応式
[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]

参加物

4

反応物 2

HCID 66221Triethyl orthoacetateHCID 597325003-Iodo-4-methylbenzohydrazide

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a59ed7b6760e45f59b06d99d623f4516
出典データセット
uspto-grants-2014_07
特許番号
US08772288B2

関連ノート

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