Chlorosuccinimide → 5-Chloro-2-(3,4,4-trifluoro-3-butenylthio)thiazole

HRID 1582175Notes

Reaction equation

HRID 1582175 reaction equation
[F:1][C:2](=[C:11]([F:13])[F:12])[CH2:3][CH2:4][S:5][C:6]1[S:7][CH:8]=[CH:9][N:10]=1.[Cl:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:14][C:8]1[S:7][C:6]([S:5][CH2:4][CH2:3][C:2]([F:1])=[C:11]([F:12])[F:13])=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11447455Thiazole, 2-[(3,4,4-trifluoro-3-butenyl)thio]-

Product 1

HCID 112307045-Chloro-2-(3,4,4-trifluoro-3-butenylthio)thiazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-(3,4,4-Trifluoro-3-butenylthio)thiazole (6.75 g, 30 mM) is dissolved in carbon tetrachloride (60 ml). N-chlorosuccinimide (4.8 g) is added to the solution and refluxed for 18 hours by heating. As soon as the reaction has reached room temperature, the mixture is filtered and the solvent is distilled off. The concentrate is purified by column chromatography (eluent: hexane/ethyl acetate=90/10) to obtain 5-chloro-2-(3,4,4-trifluoro-3-butenylthio)thiazole as pale yellow liquid (n20D 1.5326).

Workup

  1. temperaturerefluxed for 18 hours
  2. temperatureby heating
  3. customhas reached room temperature
  4. filtrationthe mixture is filtered
  5. distillationthe solvent is distilled off
  6. customThe concentrate is purified by column chromatography (eluent: hexane/ethyl acetate=90/10)

Sources & evidence

ORD record
ord-940390aa431f436ea10b6d9f617a339c
Source dataset
uspto-grants-2004_05
Patent number
US06734198B1

Reaction notes

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