2,4-DIBROMO-THIAZOLE-5-CARBALDEHYDE,97% synthesis
- Product Name:2,4-DIBROMO-THIAZOLE-5-CARBALDEHYDE,97%
- CAS Number:139669-95-7
- Molecular formula:C4HBr2NOS
- Molecular Weight:270.93
2295-31-0
68-12-2
139669-95-7
General procedure for the synthesis of 2,4-dibromothiazole-5-carbaldehyde from 2,4-thiazolidinedione and N,N-dimethylformamide: A mixture of thiazolidine-2,4-dione (15.0 g, 128 mmol), phosphorus tribromide (POBr3, 183.6 g, 640 mmol) and N,N-dimethylformamide (DMF, 10.8 mL, 140.9 mmol ) mixture was heated to 75°C for 1 hr and then warmed to 100°C for 5 hr. After completion of the reaction, the mixture was cooled to room temperature, diluted with dichloromethane (CH2Cl2) and washed with saturated sodium bicarbonate (NaHCO3) solution. The organic phase was separated, filtered and concentrated. The residue was ground with petroleum ether and evaporated to give 8.0 g of 2,4-dibromothiazole-5-carbaldehyde as a black solid.
2295-31-0
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139669-95-7
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Yield:-
Reaction Conditions:
with phosphorus(V) oxybromide in N,N-dimethyl-formamide at 20 - 108; for 8 h;
Steps:
18.A 2,4-dibromothiazole-5-carbaldehyde
A mixture of thiazolidine-2,4-dione (4.54 g, 34.88 mmol) and phosphorus oxybromide (50 g, 174.4 mmol) was treated with DMF (3.05 mL, 39.41 mmol), stirred at room temperature for 30 minutes, heated at 80° C. for 30 minutes, heated at 108° C. until hydrogen bromide evolution ceased (approximately 7 hours), cooled to room temperature, treated with ice/water (300 mL), and extracted with dichloromethane. The extract was washed with 5% aqueous NaHCO3 and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 98:2 hexanes/ethyl acetate to provide the desired product.
References:
Ma, Zhenkun;Phan, Ly Tam;Clark, Richard F.;Zhang, Suoming;Djuric, Stevan US2006/166906, 2006, A1 Location in patent:Page/Page column 26