Potassium Carbonate → 2-acetylamino-5-(1-methyl-1H-tetrazol-5-ylthio)thiazole

HRID 2380624Notes

Reaction equation

[C:1]([NH:4][C:5]1[S:6][C:7](Cl)=[CH:8][N:9]=1)(=[O:3])[CH3:2].[SH:11][C:12]1[N:16]([CH3:17])[N:15]=[N:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][C:7]([S:11][C:12]2[N:16]([CH3:17])[N:15]=[N:14][N:13]=2)=[CH:8][N:9]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2-acetylamino-5-chlorothiazole (1.76 g), 5-mercapto1-methyl-1H-tetrazole (1.2 g) and potassium carbonate (2 g) in N,N-dimethylformamide (40 ml) was heated at 130° C. for 3 hours with stirring. The reaction mixture was concentrated under reduced pressure and the residue was triturated with water. The precipitates were collected by filtration, washed with water and dried vacuo to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 150 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-5-(1-methyl-1H-tetrazol-5-ylthio)thiazole (2.1 g, yield: 82.0%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was triturated with water
filtrationThe precipitates were collected by filtration
washwashed with water
customdried vacuo
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-d61c6181f7fd4d6ca037dff452a7ecca
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05369107

Reaction notes

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