Benzyl mercaptan → 2-(Benzylsulfanyl)-4-chloro-1,3-thiazole

HRID 2073691Notes

Reaction equation

HRID 2073691 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[Na].Cl[C:14]1[S:15][CH:16]=[C:17]([Cl:19])[N:18]=1>C(O)C>[Cl:19][C:17]1[N:18]=[C:14]([S:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:15][CH:16]=1

Participants

6

Reactant 4

HCID 7509Benzyl mercaptanHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 123331552,4-Dichlorothiazole

Product 1

HCID 150771182-(Benzylsulfanyl)-4-chloro-1,3-thiazoleYield 90.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzylmercaptan (24.8 g) was added dropwise to a solution of 10.8 g of sodium methoxide in 100 ml ethanol. After stirring 15 minutes, the ehtanolic solution of sodium benzylmercaptide was added dropwise to a solution of 30.8 g 2,4-dichlorothiazole [prepared by the method of P. Reynaud et al., Bull. Soc. Chim. France, 1735 (1962)], resulting in a temperature increase of 28° to 48°. When the exotherm subsided, the suspension was refluxed 1 hour, then the solvent was evaporated. Cold water (300 ml) was added to the oily residue, and the aqueous mixture was extracted with methylene chloride. The organic solution was washed with water, followed by saturated brine, then dried over magnesium sulfate, filtered and the solvent evaporated to give 43.8 g of 4-chloro-2-phenylmethylthiothiazole as a brown oil.

Workup

  1. customprepared by the method of P
  2. customFrance, 1735 (1962)], resulting in a temperature
  3. temperatureincrease of 28° to 48°
  4. temperaturethe suspension was refluxed 1 hour
  5. customthe solvent was evaporated
  6. additionCold water (300 ml) was added to the oily residue
  7. extractionthe aqueous mixture was extracted with methylene chloride
  8. washThe organic solution was washed with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customthe solvent evaporated

Sources & evidence

ORD record
ord-53824bcdad5d4f6f937ea755f7465ea1
Source dataset
uspto-grants-1990_04
Patent number
US04919706

Reaction notes

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