Thionyl Chloride → 2-Chloromethyl-8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine

HRID 1369588Notes

Reaction equation

[CH3:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH3:17])=[C:13]([CH2:15]O)[N:14]=2)[CH:9]=[CH:10][CH:11]=1.S(Cl)([Cl:25])=O>C(Cl)Cl>[CH3:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH3:17])=[C:13]([CH2:15][Cl:25])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 8-(2,6-dimethylbenzylamino)-2-hydroxymethyl-3-methylimidazo[1,2-a]pyridine (1.0 g, 3.4 mmol) in methylene chloride (50 ml) was added dropwise thionyl chloride (0.5 g, 3.4 mmol) solved in methylene chloride (10 ml) at 5° C. The reaction mixture was stirred 2 h. at 5° C. To the mixture was washed with a saturated bicarbonate solution, the organic layer was separated, dried (Na2SO4) and evaporated under reduced pressure to give 1.0 g (93%) of the title compound.

Workup

washTo the mixture was washed with a saturated bicarbonate solution
customthe organic layer was separated
dry with materialdried (Na2SO4)
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-2ef460b228274f558630731853da9172
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06579884B1

Reaction notes

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