1-Hydroxybenzotriazole → HCID 57959389, compound

To a mixture consisting of 6-bromonicotinic acid (Sigma-Aldrich, 1.5 g), N,N-dicyclohexylcarbodiimide (1.60 g), and dichloromethane (10 mL) was added a solution consisting of veratrylamine (1.24 g) in dichloromethane (10 mL) followed by addition of 1-hydroxybenzotriazole (100 mg). The reaction mixture was stirred overnight at room temperature. The crude reaction mixture was diluted with added dichloromethane (200 mL) and the diluted mixture was washed twice with water (2×100 mL) and once with brine solution (100 mL). The organic phase was subsequently dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide a white solid. The product was triturated in ethyl acetate and collected by filtration to afford the title intermediate as a white solid (2.22 g, 85% yield); Rf 0.35 with 3:2 v/v hexanes-ethyl acetate; MS (ESI−) m/z 349, 351.

1. additionwas added a solution
2. customThe crude reaction mixture
3. washthe diluted mixture was washed twice with water (2×100 mL) and once with brine solution (100 mL)
4. dry with materialThe organic phase was subsequently dried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customto provide a white solid
8. customThe product was triturated in ethyl acetate
9. filtrationcollected by filtration

ORD record

ord-b6506ebf3d034935b87331ac18176021

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08440417B2