Sulfuryl chloride → 2-Chloro-5-(chloromethyl)-1,3-thiazole--hydrogen chloride (1/1)

HRID 725206Notes

Reaction equation

HRID 725206 reaction equation
[Cl:1][CH2:2][CH:3]=[CH:4][N:5]=[C:6]=[S:7].S(Cl)([Cl:11])(=O)=O>ClCCCl>[ClH:1].[Cl:11][C:6]1[S:7][C:3]([CH2:2][Cl:1])=[CH:4][N:5]=1

Participants

4

Conditions

Temperature
25 °C

Procedure

To a solution of 45 g of 3-chloroprop-1-enyl isothiocyanate in 90 ml of 1,2-dichloroethane, 50.5 g of sulphuryl chloride was added over 10 hours at -10° C. The reaction mixture was allowed to warm to 25° C. overnight, to complete the reaction. The solution was cooled to -15° C. and the product, a pale yellow solid, was isolated by filtration and washed with hexane. 38.2 g of 2-chloro-5-(chloromethyl) thiazole hydrochloride was thus obtained, having a melting point of 59°-61° C. and being a yield of 61.6%.

Workup

  1. customthe reaction
  2. temperatureThe solution was cooled to -15° C.
  3. customthe product, a pale yellow solid, was isolated by filtration
  4. washwashed with hexane

Sources & evidence

ORD record
ord-896c39ed1fdd4775a7cc875d55948e95
Source dataset
uspto-grants-1998_01
Patent number
US05705652

Reaction notes

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