Sulfuryl chloride → HCID 11021483, compound

HRID 1954450Notes

Reaction equation

HRID 1954450 reaction equation
[CH2:1]([S:8][C:9](=[S:15])[NH:10][CH2:11][C:12](Cl)=[CH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].S(Cl)([Cl:24])(=O)=O>ClCCl>[CH2:1]([S:8][C:9]1[S:15][C:12]([CH2:13][Cl:24])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 54395229Benzyl (2-chloroprop-2-en-1-yl)carbamodithioate

Product 1

HCID 11021483HCID 11021483, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5.0 g of (2-chloro-allyl)-dithiocarbamic acid benzyl ester and 4.1 g of sodium hydrogen carbonate are placed in 100 ml of dichloromethane and cooled in an ice bath. In the course of 3 minutes, a solution of 3.2 g of sulfuryl chloride in 10 ml of dichloromethane is added, and when the addition is complete the ice bath is removed. The mixture is stirred at room temperature for 2 hours and filtered off with suction, and the filtrate is concentrated by evaporation. The residue crystallises after the addition of diethyl ether. Filtration yields 2-benzylsulfanyl-5-chloromethyl-thiazole having a melting point of 129-131° C. in the form of the hydrochloride. Extraction of the mother liquor with semi-saturated aqueous sodium hydrogen carbonate solution and removal of the ether by distillation yield 2-benzylsulfanyl-5-chloromethyl-thiazole having a melting point of 57-61° C.

Workup

  1. temperaturecooled in an ice bath
  2. additionwhen the addition
  3. customis removed
  4. filtrationfiltered off with suction
  5. concentrationthe filtrate is concentrated by evaporation
  6. customThe residue crystallises
  7. additionafter the addition of diethyl ether
  8. filtrationFiltration

Sources & evidence

ORD record
ord-e069dca12b804e51970e65c9587c4198
Source dataset
uspto-grants-2000_09
Patent number
US06121455

Reaction notes

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