1,3-Dichloroacetone → HCID 19367122, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][N:3]=1.[Cl:10][CH2:11][C:12]([CH2:14]Cl)=O>C(COC)OC>[Cl:10][CH2:11][C:12]1[N:1]=[C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][N:3]2[CH:14]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2-amino-5-methoxypyridine (0.5036 g; prepared by the method of Lombardino, J. Med. Chem. 1981, 24 39-42), 1,3-dichloroacetone (Aldrich; 0.3935 g), and dimethoxyethane (2.5 mL) is stirred overnight at room temperature. The mixture is concentrated under reduced pressure and ethanol (7.9 mL) is added. After the mixture has stirred for 30 min at 80° C., it is cooled and concentrated under reduced pressure. The residue is partitioned between dichloromethane and saturated aq. sodium bicarbonate and the combined organic layers are dried with MgSO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (4/96) to give 0.1392 g of 2-(chloromethyl)-6-methoxyimidazo[1,2-a]pyridine; 1H NMR (CDCl3) δ 3.82, 4.75, 6.99, 7.48, 7.56, 7.59.