Dimethylformamide → 5-Bromo-1,3-thiazole-2-carboxamide

To 5-bromo-thiazole-2-carboxylic acid (0.267 g, 0.128 mmol) suspended in dry dichloromethane (30 mL) are added oxalyl chloride (0.22 mL, 0.257 mmol) and a drop of DMF. The reaction is stirred for 1 hour at room temperature. The solvent is evaporated and the resultant crude is dissolved in 7M NH3 in MeOH. The reaction mixture is stirred overnight at room temperature. After evaporation of the solvent, the residue is dissolved in dichloromethane and washed with 1M NaOH. The organic phase is dried over MgSO4, filtered and evaporated. The residue is purified by silica gel column chromatography eluting with 95:5 DCM:MeOH to give the title compound (33.8 mg, 25%).

1. customThe solvent is evaporated
2. dissolutionthe resultant crude is dissolved in 7M NH3 in MeOH
3. stirringThe reaction mixture is stirred overnight at room temperature
4. customAfter evaporation of the solvent
5. dissolutionthe residue is dissolved in dichloromethane
6. washwashed with 1M NaOH
7. dry with materialThe organic phase is dried over MgSO4
8. filtrationfiltered
9. customevaporated
10. customThe residue is purified by silica gel column chromatography
11. washeluting with 95:5 DCM

ORD record

ord-7293626005254b3e83754a69c1ca3320

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173656B2