Thionyl Chloride → 1-(4-(chloromethyl)thiazol-2-yl)-N,N-dimethylmethanamine hydrochloride

HRID 1632233Notes

Reaction equation

HRID 1632233 reaction equation
[ClH:1].[CH3:2][N:3]([CH2:5][C:6]1[S:7][CH:8]=[C:9]([CH2:11]O)[N:10]=1)[CH3:4].S(Cl)([Cl:15])=O>C(Cl)(Cl)Cl>[ClH:15].[CH3:2][N:3]([CH2:5][C:6]1[S:7][CH:8]=[C:9]([CH2:11][Cl:1])[N:10]=1)[CH3:4]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 13121938(2-Dimethylaminomethyl-thiazol-4-yl)-methanol hydrochloride

Product 1

HCID 131219581-(4-(chloromethyl)thiazol-2-yl)-N,N-dimethylmethanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The methanols produced by the process of this example are readily converted to the corresponding thiazolemethyl chlorides according to the following procedure: A suspension was prepared from 1.05 grams of 2-dimethylaminomethyl-4-thiazolemethanol hydrochloride and 15 ml. of chloroform. Thionyl chloride (2.50 g) was added and the resulting mixture was stirred at reflux temperature for about 2.75 hours. Any volatile constituents including excess thionyl chloride were removed by evaporation. The residue was suspended in chloroform and the chloroform removed by evaporation. The residue was then recrystallized from a methanol-ethyl acetate solvent mixture to yield 2-dimethylaminomethyl-4-thiazolylmethylchloride hydrochloride melting at 136°-8° C.

Workup

  1. temperatureat reflux temperature for about 2.75 hours
  2. customwere removed by evaporation
  3. customthe chloroform removed by evaporation
  4. customThe residue was then recrystallized from a methanol-ethyl acetate solvent mixture

Sources & evidence

ORD record
ord-c88e21ac9e804da78a04aff902f80ba2
Source dataset
uspto-grants-1984_10
Patent number
US04474794

Reaction notes

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