Tert-Butylamine → 5-bromo-N-tert-butylthiophene-2-carboxamide

A mixture of 5-bromothiophene-2-carboxylic acid (10.0 g, 48 mmol) and thionyl chloride (3.5 ml, 48 mmol) was boiled under reflux for 3 hrs. Excess of thionyl chloride was removed by distillation under reduced pressure. The residue was taken up in DCM (30 ml) and a solution of tert-butylamine (7.0 g, 96 mmol) in DCM (30 ml) was added with stirring, the temperature of the mixture being kept below 10° C. The resulting solution was stirred at 25° C. for 12 hrs, washed with water (3×20 ml) and dried over MgSO4. The combined washings were basified to pH11 with 5M KOH(aq) and extracted with DCM (3×100 ml) and dried over MgSO4. The combined organic solutions were evaporated under reduced pressure to give the crude product (12.5 g). Recrystallization from (C6H12/CHCl3) gave the pure amide (10.5 g) as a white solid. MS (ES+): 263 (M+H)+.

1. temperatureunder reflux for 3 hrs
2. customExcess of thionyl chloride was removed by distillation under reduced pressure
3. custombeing kept below 10° C
4. stirringThe resulting solution was stirred at 25° C. for 12 hrs
5. washwashed with water (3×20 ml)
6. dry with materialdried over MgSO4
7. extractionextracted with DCM (3×100 ml)
8. dry with materialdried over MgSO4
9. customThe combined organic solutions were evaporated under reduced pressure
10. customto give the crude product (12.5 g)
11. customRecrystallization from (C6H12/CHCl3)

ORDレコード

ord-63d86ef3e24a466091311811481632d8

出典データセット

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07745449B2