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

HRID 650872

반응식

HRID 650872 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3007855Zincchloride촉매

반응 조건

온도
1700 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-31e430c6e4b54575a467daf2d48b7361
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06277790B1

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