Chlorobenzene → HCID 11021483, compound

HRID 1954449Notes

Reaction equation

HRID 1954449 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+].[Cl:21]C1C=CC=CC=1>>[CH2:1]([S:8][C:9]1[S:15][C:12]([CH2:13][Cl:21])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7964ChlorobenzeneHCID 516892Sodium BicarbonateHCID 54395229Benzyl (2-chloroprop-2-en-1-yl)carbamodithioate

Product 1

HCID 11021483HCID 11021483, compound

Conditions

Temperature
5.5 °C

Procedure

Under a slight stream of nitrogen, 35.8 g of (2-chloro-allyl)-dithiocarbamic acid benzyl ester and 31.8 g of sodium hydrogen carbonate are placed in 250 ml of chlorobenzene. The mixture is then cooled to 5-6° C. The apparatus is flushed thoroughly with nitrogen. Then 28.2 g of sulfuryl chloride are added in the course of 120 minutes in such a manner that the temperature can be maintained at 5-10° C. When the addition is complete, stirring is carried out for about 20 minutes. The reaction mixture is filtered off with suction, the filtration residue is washed with 20 ml of chlorobenzene, and the filtrate is thoroughly degassed in vacuo at 20-25° C. Then the solvent is removed by distillation at 30° C. under reduced pressure. 90 ml of hexane are added to the residue. Seeding is carried out, then the mixture is stirred at about 0° C. and about 0.8 g of hydrogen chloride gas is introduced until the solution will take up no more gas. The mixture is stirred for a further 15 minutes, the crude product is filtered off at 0-5° C., and the filtration residue is washed with 10 ml of hexane and dried in vacuo. In that manner 2-benzylsulfanyl-5-chloromethyl-thiazole is obtained in the form of the hydrochloride.

Workup

  1. customThe apparatus is flushed thoroughly with nitrogen
  2. additionThen 28.2 g of sulfuryl chloride are added in the course of 120 minutes in such a manner that the temperature
  3. temperaturecan be maintained at 5-10° C
  4. additionWhen the addition
  5. filtrationThe reaction mixture is filtered off with suction
  6. washthe filtration residue is washed with 20 ml of chlorobenzene
  7. customthe filtrate is thoroughly degassed in vacuo at 20-25° C
  8. customThen the solvent is removed by distillation at 30° C. under reduced pressure
  9. addition90 ml of hexane are added to the residue
  10. stirringthe mixture is stirred at about 0° C.
  11. additionabout 0.8 g of hydrogen chloride gas is introduced until the solution
  12. stirringThe mixture is stirred for a further 15 minutes
  13. filtrationthe crude product is filtered off at 0-5° C.
  14. washthe filtration residue is washed with 10 ml of hexane
  15. customdried in vacuo

Sources & evidence

ORD record
ord-7fdf50f84013432e9293dc8804767117
Source dataset
uspto-grants-2000_09
Patent number
US06121455

Reaction notes

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