Dimethyl Sulfide → 2-Methylthiomethyl-3,4,6-trifluoroaniline

HRID 486251

Reaction equation

HRID 486251 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[C:6]([F:10])=[CH:5][C:3]=1[NH2:4].[CH3:11][S:12][CH3:13].ClN1C(=O)CCC1=O.[OH-].[Na+]>C(N(CC)CC)C.ClCCl>[CH3:11][S:12][CH2:13][C:5]1[C:6]([F:10])=[C:7]([F:9])[CH:8]=[C:2]([F:1])[C:3]=1[NH2:4]

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 949532,4,5-Trifluoroaniline

Product 1

HCID 189744612-Methylthiomethyl-3,4,6-trifluoroaniline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To 2,4,5-trifluoroaniline (35.0 g) are added anhydrous dichloromethane (530 ml) and dimethyl sulfide (24.6 ml) and the mixture is cooled to 0° C. Thereto N-chlorosuccinimide (38.2 g) is gradually added below 5° C. After the mixture is stirred at the same temperature for 15 minutes, triethylamine (47.7 ml) is gradually added. After reflux for 12 hours, the resultant is made alkaline with 5 % aqueous sodium hydroxide solution, extracted with dichloromethane, and the extract is dried over sodium sulfate and concentrated. The residue is purified with column chlomatography (silica-gel, dichloromethane: n-hexane=1:4) to give 2-methylthiomethyl-3,4,6-trifluoroaniline (22.3 g).

Workup

  1. customis gradually added below 5° C
  2. temperatureAfter reflux for 12 hours
  3. extractionextracted with dichloromethane
  4. dry with materialthe extract is dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified with column chlomatography (silica-gel, dichloromethane: n-hexane=1:4)

Sources & evidence

ORD record
ord-2f6f9312ebd24cbba8a1b468f2491aed
Source dataset
uspto-grants-1994_03
Patent number
US05290934

Linked notes

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