Thionyl Chloride → HCID 19883468, compound

HRID 345520Notes

Reaction equation

HRID 345520 reaction equation
[ClH:1].[CH3:2][C:3]1[N:4]=[C:5]2[CH:10]=[C:9]([CH2:11]O)[CH:8]=[CH:7][N:6]2[CH:13]=1.S(Cl)([Cl:16])=O>ClC(Cl)Cl>[ClH:16].[Cl:1][CH2:11][C:9]1[CH:8]=[CH:7][N:6]2[CH:13]=[C:3]([CH3:2])[N:4]=[C:5]2[CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19883453HCID 19883453, compound

Product 1

HCID 19883468HCID 19883468, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 10.7 parts of 2-methylimidazo[1,2-a]pyridine-7-methanol monohydrochloride and 150 parts of trichloromethane were added dropwise 9.6 parts of thionyl chloride. The resulting solution was stirred for 15 minutes at room temperature. The reaction mixture was evaporated in vacuo and the residue was stirred in 80 parts of 2-propanone. The product was filtered off, washed with 2,2'-oxybispropane and dried, yielding 11.8 parts (100%) of 7-(chloromethyl)-2-methylimidazo[1,2-a]pyridine monohydrochloride; mp. 178.5 (intermediate 16).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. stirringthe residue was stirred in 80 parts of 2-propanone
  3. filtrationThe product was filtered off
  4. washwashed with 2,2'-oxybispropane
  5. customdried

Sources & evidence

ORD record
ord-0fb413a8caff420284ee87d4bfa400a9
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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