Dimethyl Sulfide → HCID 23359001, compound

HRID 2396941Notes

Reaction equation

HRID 2396941 reaction equation
[F:1][C:2]1[C:8]([CH3:9])=[C:7]([F:10])[C:6]([F:11])=[CH:5][C:3]=1[NH2:4].[CH3:12][S:13][CH3:14].ClN1C(=O)CCC1=O.[OH-].[Na+]>C(N(CC)CC)C.ClCCl>[F:1][C:2]1[C:8]([CH3:9])=[C:7]([F:10])[C:6]([F:11])=[C:5]([CH2:12][S:13][CH3:14])[C:3]=1[NH2:4]

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 146512532,4,5-Trifluoro-3-methylaniline

Product 1

HCID 23359001HCID 23359001, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To anhydrous dichloromethane (170 ml) are added 2,4,5-trifluoro-3-methylaniline (16.89 g) and dimethyl sulfide (11 ml). Thereto N-chlorosuccinimide (17.2 g) is added gradually below 5° C. After stirring for 30 minutes, triethylamine (21 ml) is added dropwise and the mixture is refluxed over night. After the mixture is cooled and made alkaline with 5% aqueous sodium hydroxide solution, the resultant is extracted with dichloromethane, and the extract is washed with water and dried. The solvent is distilled off under reduced pressure and the residue is purified by silica-gel column-chromatography (dichloromethane : n-hexane =1 : 1) to give 2,4,5-trifluoro-3-methyl-6-methylthiomethylaniline (8.3 g).

Workup

  1. temperaturethe mixture is refluxed over night
  2. temperatureAfter the mixture is cooled
  3. extractionthe resultant is extracted with dichloromethane
  4. washthe extract is washed with water
  5. customdried
  6. distillationThe solvent is distilled off under reduced pressure
  7. customthe residue is purified by silica-gel column-chromatography (dichloromethane : n-hexane =1 : 1)

Sources & evidence

ORD record
ord-306ef78ba97d4cb4ad78d3e6aeec7f34
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

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