Potassium Carbonate → 2-Acetylamino-4-hydroxymethyl-5-(4-pyridylthio)thiazole

HRID 1656975Notes

Reaction equation

[C:1]([NH:4][C:5]1[S:6][C:7](Cl)=[C:8]([CH2:10][OH:11])[N:9]=1)(=[O:3])[CH3:2].[SH:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][C:7]([S:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:8]([CH2:10][OH:11])[N:9]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-acetylamino-5-chloro-4-hydroxymethylthiazole (1 g), 4-mercaptopyridine (0.6 g) and potassium carbonate (1 g) in N,N-dimethylformamide (20 ml) was heated at 110° C. for 8 hours with stirring. The reaction mixture was poured into ice water and filtered by suction. The filtrate was extracted with a mixture of ethyl acetate and tetrahydrofuran (1:1) and dried over magnesium sulfate. The solvent was concentrated under reduced pressure to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 75 g) and eluted with a mixture of chloroform and methanol (10:1). The fractions containing the objective compound were combined and concentrated under reduced pressure to give 2-acetylamino-4-hydroxymethyl-5-(4-pyridylthio)thiazole (0.90 g, yield: 64.3%). mp: 220°-222° C. (dec.)

Workup

filtrationfiltered by suction
extractionThe filtrate was extracted with a mixture of ethyl acetate and tetrahydrofuran (1:1)
dry with materialdried over magnesium sulfate
concentrationThe solvent was concentrated under reduced pressure
customto give solid
washeluted with a mixture of chloroform and methanol (10:1)
additionThe fractions containing the objective compound
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-064a89d5b89a4307b8d9b4f4b7bc9616
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05256675

Reaction notes

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