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ChemicalBook CAS DataBase List 5-Thiazolamine, 2-methyl-

5-Thiazolamine, 2-methyl- synthesis

3synthesis methods
-

Yield: 52%

Reaction Conditions:

Stage #1:cyanomethylamine sulfate with triethylamine in methanol at 0; for 0.5 h;
Stage #2:ethyl dithioacetate in methanol at 20; for 2 h;

Steps:

2
Method 2; 2-Methγl- 1 ,3-thiazol-5-amine; To a solution of aminoacetonitrile bisulfate (6.4 g, 41.6 mmol) in anhydrous MeOH (75 ml) at O0C was added Et3N (11.6 mL, 83mmol). After 30 minutes, ethyl dithioacetate (5g, 41.6 mmol) was added and the resulting dark orange solution stirred at room temperature for 2 hours. Half the solvent was removed under reduced pressure. The solution was diluted with an equivalent volume of EtOAc, washed with water, and dried (Na2SO4). The solvents were removed under reduced pressure and the residue slurried in warm EtOAc, cooled in an ice bath, and filtered to give 2.45g (52%) of a brown solid. 1H NMR DMSO-d6: 6.62 (s, 1 H) 5.36 (bs, 2 H) 2.89 (s, 3 H); m/z: 115.

References:

ASTRAZENECA AB;ASTRAZENECA UK LIMITED WO2007/71955, 2007, A1 Location in patent:Page/Page column 48

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