Acetyl chloride → 5-acetyl-4H,5H,6H,7H-thieno[3,2-c]pyridine-2-carbaldehyde
Reaction equation
Cl.[S:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[C:3]1[CH:11]=[O:12].[C:13](Cl)(=[O:15])[CH3:14]>C(Cl)Cl>[C:13]([N:7]1[CH2:8][CH2:9][C:10]2[S:2][C:3]([CH:11]=[O:12])=[CH:4][C:5]=2[CH2:6]1)(=[O:15])[CH3:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a cold (0° C.) suspension of 1.5 g. (7.4 mmol) of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carbaldehyde hydrochloride in 50 mL methylene chloride, under N2 atm., dry conditions, was added dropwise under stirring 2.6 mL (2.5 eqs) of triethylamine. RM stirred for 30 min at 0° C. and a solution of 0.7 g. (8.1 mmol, 1.1 eqs) of acetyl chloride in 15 mL methylene chloride was dropwise added, RM allowed to reach RT and stirred for 3 hours. Filtered trough a celite pad, filtrate washed with 3×50 mL water, dried, evaporated, gave 1.1 g. (71.4%) of the title compound, viscous oil, (M+H)+ 210.3.