Propylamine → 2,4-Dimethylthiophen-3-yl-(n-propyl)amine

HRID 650872ノート

反応式

HRID 650872 の反応式
[CH2:1]([NH2:4])[CH2:2][CH3:3].[CH3:5][C:6]1[S:7][CH:8]=[C:9]([CH3:12])[C:10]=1O.[OH-].[Na+]>[Cl-].[Zn+2].[Cl-]>[CH3:5][C:6]1[S:7][CH:8]=[C:9]([CH3:12])[C:10]=1[NH:4][CH2:1][CH2:2][CH3:3]

参加物

5

反応物 3

HCID 7852PropylamineHCID 14798Sodium HydroxideHCID 863643-Hydroxy-2,4-dimethylthiophene

生成物 1

HCID 217099312,4-Dimethylthiophen-3-yl-(n-propyl)amine

試薬・触媒・溶媒 1

HCID 3007855Zincchloride触媒

反応条件

温度
1700 °C

実験手順

In an atmosphere of inert gas, 34.6 g (0.59 mol) of propylamine were admixed with 10.6 g (78 mmol) of anhydrous zinc chloride powder in the course of which the temperature of the mixture rose strongly. The solution was then admixed with 50 g (0.39 mol) of 2,4-dimethyl-3-hydroxythiophene, introduced into an autoclave and heated at 1700° C. under pressure (approximately 5 bar) for 16 hours. After cooling, the mixture was made alkaline using 50 ml of 33% strength aqueous sodium hydroxide solution and extracted twice with hexane, the combined organic phases were washed three times with water, dried over magnesium sulfate, filtered and concentrated under water pump vacuum, and the residue was distilled. Yield 31.2 g (47%), b.p. 88° C. (2 mbar). 1H NMR (270 MHz in CDCl3):δ=0.96 (t, 3H), 1.56 (sext., 2H), 2.12 (s, 3H), 2.31 (s, 3H), 2.96 (t, 2H), 3.18 (s, 1H), 6.61 (s, 1H).

後処理

  1. additionintroduced into an autoclave
  2. temperatureAfter cooling
  3. extractionextracted twice with hexane
  4. washthe combined organic phases were washed three times with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under water pump vacuum
  8. distillationthe residue was distilled

出典と根拠

ORDレコード
ord-31e430c6e4b54575a467daf2d48b7361
出典データセット
uspto-grants-2001_08
特許番号
US06277790B1

反応ノート

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