Thionyl Chloride → 6-(Chloromethyl)-2-(2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine

HRID 2272830Notes

Reaction equation

HRID 2272830 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:19]=[C:12]2[CH:13]=[CH:14][C:15]([CH2:17]O)=[CH:16][N:11]2[N:10]=1.O=S(Cl)[Cl:22]>>[Cl:22][CH2:17][C:15]1[CH:14]=[CH:13][C:12]2[N:11]([N:10]=[C:9]([C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=3[CH3:8])[N:19]=2)[CH:16]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 118129975(2-(2,6-Dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl)methanol

Product 1

HCID 1181300036-(Chloromethyl)-2-(2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridineYield 100%

Procedure

A solution of [2-(2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]methanol (0.17 g, 0.67 mmol) in SOCl2(2.0 mL) is stirred for 2 hours at room temperature. The reaction mixture is evaporated to dryness and co-distilled with toluene to give the title compound as a yellow solid (0.198 g, 100% crude) which is used without further purification. LCMS m/z 272 (M+H)+.

Workup

  1. customThe reaction mixture is evaporated to dryness and co-distilled with toluene

Sources & evidence

ORD record
ord-af2e6ee6ebef423a9e6d3333135fea7b
Source dataset
uspto-grants-2015_09
Patent number
US09120793B2

Reaction notes

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