p-Toluenesulfonic acid → N-(2-hydroxy-3-n-propyl-4-methoxybenzoyl)thiazolidine

HRID 465914노트

반응식

HRID 465914 반응식
COC[O:4][C:5]1[C:17]([CH2:18][CH2:19][CH3:20])=[C:16]([O:21][CH3:22])[CH:15]=[CH:14][C:6]=1[C:7]([N:9]1[CH2:13][CH2:12][S:11][CH2:10]1)=[O:8].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.O>[OH:4][C:5]1[C:17]([CH2:18][CH2:19][CH3:20])=[C:16]([O:21][CH3:22])[CH:15]=[CH:14][C:6]=1[C:7]([N:9]1[CH2:13][CH2:12][S:11][CH2:10]1)=[O:8]

참가 물질

5

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 14719505N-(2-methoxymethoxy-3-n-propyl-4-methoxybenzoyl)thiazolidine

생성물 1

HCID 14719506N-(2-hydroxy-3-n-propyl-4-methoxybenzoyl)thiazolidine수율 93.8%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

The N-(2-methoxymethoxy-3-n-propyl-4-methoxybenzoyl)thiazolidine (9.0 g) was dissolved in a solution of methanol (100 ml)-water (20 ml). To the solution was added p-toluenesulfonic acid (2 spoonfuls in spatula) and the mixture was agitated at 60° C. for 23 hours. The reaction mixture was concentrated in evacuated atomosphere to about one fourth of the original volume. Saturated aqueous solution of sodium bicarbonate was added to the concentrate, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated in evacuated atomosphere. The residue was subjected to column chromatography using silica gel, and there was obtained N-(2-hydroxy-3-n-propyl-4-methoxybenzoyl)thiazolidine (7.3 g) from fractions eluted with n-hexane-ethyl acetate (5:1).

후처리

  1. concentrationThe reaction mixture was concentrated in evacuated atomosphere to about one fourth of the original volume
  2. additionSaturated aqueous solution of sodium bicarbonate was added to the concentrate
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in evacuated atomosphere

출처 및 근거

ORD 기록
ord-47637f04ae004b55b5939e8662ce861e
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155106

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