ChemicalBook CAS DataBase List 2-Thiazolamine, 5-(1-methylethyl)-

2-Thiazolamine, 5-(1-methylethyl)- synthesis

6synthesis methods

Product Name:2-Thiazolamine, 5-(1-methylethyl)-
CAS Number:101080-15-3
Molecular formula:C6H10N2S
Molecular Weight:142.22

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590-86-3 Synthesis

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101080-15-3
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$53.00/25 mg

Yield: 42%

Reaction Conditions:

with bromine;thiourea in 1,4-dioxane;ethanol;dichloromethane

Steps:

4 Preparation of a Compound of Formula (II): 2-amino-5-isopropyl-1,3-thiazole
EXAMPLE 4 Preparation of a Compound of Formula (II): 2-amino-5-isopropyl-1,3-thiazole 3-Methylbutanaldehyde (2 ml; 18.6 mmol) was dissolved in 15 ml of dioxane. A solution 2% v/v of bromine in dioxane (47.81 ml; 18.6 mmol) was dropped therein at 0° C. The mixture was maintained at room temperature under stirring for 2 hours, then 2.83 g (37.2 mmol) of thiourea and 10 ml of ethanol were added. After 6 hours at room temperature the solution was evaporated to dryness, the residue was dissolved in methylene chloride and the product extracted with 1M hydrochloric acid; the aqueous layer was made basic by using 30% ammonium hydrate and extracted again with methylene chloride. The organic phase was dried over sodium sulfate and evaporated under vacuum. The residue was chromatographed on a silica gel column, eluding with cyclohexane-ethylacetate to give 1.1 g (42% yield) of the title compound. ¹H-NMR (DMSO-d⁶) δppm: 6.6 (s, 2H, NH₂); 6.58 (s, 1H, thiazole CH); 2.9 (m, 1H, CHMe₂); 1.18 (s, 3H, MeCHMe); 1.17 (s, 3H, MeCHMe).

References:

Pevarello, Paolo;Amici, Raffaella;Traquandi, Gabriella;Villa, Manuela;Vulpetti, Anna;Isacchi, Antonella US2003/187040, 2003, A1