Ammonium Chloride → HCID 22617023, compound

766 mg (5 mmol) of 4-cyclobutyl-2-methylthiazole was dissolved in 15 ml of anhydrous tetrahydrofuran and mixed with 561 mg (5 mmol) of potassium tert-butoxide, and 3 ml (5 mmol) of n-butyllithium (1.68M hexane solution) was added dropwise at −78° C. After 3 hours of stirring at the same temperature, 1270 mg (6 mmol) of 3-bromomethylbenzonitrile in 3 ml anhydrous tetrahydrofuran was added dropwise, and the reaction solution was stirred for one hour and 40 minutes. After addition of saturated aqueous ammonium chloride, the reaction solution was extracted with diethyl ether twice, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo for removal of the solvent. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=4:1) to give 876 mg of the title compound as a yellow oily substance in a yield of 64%.

1. additionwas added dropwise at −78° C
2. additionwas added dropwise
3. extractionthe reaction solution was extracted with diethyl ether twice
4. washthe organic layer was washed with saturated aqueous sodium chloride
5. dry with materialdried over anhydrous magnesium sulfate
6. customevaporated in vacuo for removal of the solvent
7. customThe residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=4:1)

ORD record

ord-155388ce7550418c8d5fae6ed155d39a

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06376671B1