Sodium methanethiolate → 4-Methyl-5-(methylsulfanyl)-1,3-thiazol-2-amine

HRID 1009057Notes

Reaction equation

HRID 1009057 reaction equation
Br[C:2]1[S:6][C:5]([NH2:7])=[N:4][C:3]=1[CH3:8].[CH3:9][S-:10].[Na+]>CO>[CH3:8][C:3]1[N:4]=[C:5]([NH2:7])[S:6][C:2]=1[S:10][CH3:9]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 129543735-Bromo-4-methyl-1,3-thiazol-2-amine

Product 1

HCID 187352644-Methyl-5-(methylsulfanyl)-1,3-thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Bromo-4-methyl-thiazol-2-ylamine (1.35 g, 7 mmol,) was dissolved in methanol abs. (13.5mL) and sodium methanethiolate (0.6 g, 7.7 mmol) 1.1 equiv.) was added portionwise at rt. After stirring overnight, the dark colored mixture was concentrated under reduced pressure and purified over a 50 g silica cartridge (NH2-modified) with ethyl acetate as eluent. The desired fractions were evaporated to give the title compound as a light yellow solid: 180 mg, MS (ISP): m/e 161.1 (M+H)+

Workup

  1. concentrationthe dark colored mixture was concentrated under reduced pressure
  2. custompurified over a 50 g silica cartridge (NH2-modified) with ethyl acetate as eluent
  3. customThe desired fractions were evaporated

Sources & evidence

ORD record
ord-99a3bb1bee3d470295e3d3edce32c9b4
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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