Thionyl Chloride → HCID 20144954, compound

HRID 648598Notes

Reaction equation

HRID 648598 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][NH:6][C:7]1[S:8][C:9]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:10]([CH2:12]O)[N:11]=1>C(Cl)(Cl)Cl>[CH3:5][NH:6][C:7]1[S:8][C:9]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:10]([CH2:12][Cl:3])[N:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20144957HCID 20144957, compound

Product 1

HCID 20144954HCID 20144954, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of thionylchloride (1.06 g) in chloroform (5 ml) was dropwise added to a solution of 2-methylamino-4-hydroxymethyl-5-(4-pyridyl)thiazole (1.0 g) in chloroform (20 ml) at ambient temperature for a period of 5 minutes with stirring, which was continued under the same condition for 90 minutes and at 50° C. for 30 minutes. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of water (50 ml) and ethyl acetate (30 ml). The solution was adjusted to pH 6.5 with 30% aqueous potassium carbonate and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off to give yellow powder of 2-methylamino-4-chloromethyl-5-(4-pyridyl)thiazole (0.9 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in a mixture of water (50 ml) and ethyl acetate (30 ml)
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-6e7b56187d164de9a527494b1676ca88
Source dataset
uspto-grants-1988_04
Patent number
US04735957

Reaction notes

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