Chloroform → 2-Acetylamino-4-hydroxymethyl-5-(4-pyridylthio)thiazole
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+].C(Cl)(Cl)Cl>CN(C)C=O.CO>[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
Reactant 4
Product 1
Reagents, catalysts & solvents 2
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 eluded with a mixture of chloroform and methanol (10:1l). 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%).
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
- additionThe fractions containing the objective compound
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d97fec0c4fcd4f7e93656454d16be66c
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05369107
Reaction notes
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