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

HRID 465914Notes

Reaction equation

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]

Participants

Conditions

Temperature: 60 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-47637f04ae004b55b5939e8662ce861e
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05155106

Reaction notes

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