Ethylene Glycol → 3-[3-(1,3-Dioxolan-2-yl)phenoxy]propanamine

HRID 325680노트

반응식

HRID 325680 반응식
[CH:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][N:10]1C(=O)C2C(=CC=CC=2)C1=O)=[O:2].[CH2:24](O)[CH2:25][OH:26]>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:26]1[CH2:25][CH2:24][O:2][CH:1]1[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][NH2:10]

참가 물질

5

반응물 2

HCID 174Ethylene GlycolHCID 128106403-(3-(1,3-Dioxoisoindolin-2-yl)propoxy)benzaldehyde

생성물 1

HCID 127974473-[3-(1,3-Dioxolan-2-yl)phenoxy]propanamine수율 85%

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 241Benzene용매

실험 절차

A solution of 2-[3-(3-formylphenoxy)propyl]-1H-isoindole-1,3-(2H)-dione (90 g) and p-toluenesulphonic acid, monohydrate (200 mg) in benzene (900 ml) and ethane-1,2-diol (25 g) was heated under reflux using a Dean-Stark separator for 8 h. The cooled solution was washed successively with sodium carbonate solution, water, sodium chloride solution, and evaporated in vacuo. The resulting oil was dissolved in tetrahydrofuran (1 liter) and stirred with hydrazine hydrate (50 ml) at room temperature for 24 hr. The mixture was diluted with ether and filtered. The filtrate was distilled to give the title compound as a colourless oil (55.2 g) b.p. 134°-6° (0.7 mm). TLC silica; methanol:ammonia 80:1; Rf 0.4.

후처리

  1. temperatureunder reflux
  2. customfor 8 h
  3. washThe cooled solution was washed successively with sodium carbonate solution, water, sodium chloride solution
  4. customevaporated in vacuo
  5. dissolutionThe resulting oil was dissolved in tetrahydrofuran (1 liter)
  6. additionThe mixture was diluted with ether
  7. filtrationfiltered
  8. distillationThe filtrate was distilled

출처 및 근거

ORD 기록
ord-def86e0895e9498a9071a9f3791cb42f
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04442110

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