Dimethyl Sulfide → Benzenamine, 2-(1-methylethyl)-6-[(methylthio)methyl]-

HRID 1734912Notes

Reaction equation

HRID 1734912 reaction equation
ClN1C(=O)CCC1=O.[CH:9]([C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14])([CH3:11])[CH3:10].[CH3:19][S:20][CH3:21].C(N(CC)CC)C>C(Cl)Cl.CCCCCC>[CH:9]([C:12]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][S:20][CH3:21])[C:13]=1[NH2:14])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 125612-IsopropylanilineHCID 31398Chlorosuccinimide

Product 1

HCID 10932356Benzenamine, 2-(1-methylethyl)-6-[(methylthio)methyl]-Yield 65%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

15.51 g (116 mmol) of N-chlorosuccinimide were added over a period of 20 minutes to a solution of 11.2 g (82.9 mmol) of 2-isopropylaniline and 7.22 g (116 mmol) of dimethyl sulfide in 200 ml of methylene chloride, whilst maintaining the internal temperature at between 15° and 20° C. After 15 minutes, 11.73 g (116 mmol) of triethylamine were added to the mixture, which was then heated under reflux for 9 hours. At the end of this time, the solvent was removed by distillation under reduced pressure. The resulting residue was mixed with diethyl ether and insoluble materials which appeared were filtered off. The filtrate was concentrated by evaporation under reduced pressure, and the concentrate was purified by column chromatography through 300 g of silica gel, using a gradient elution method, with mixtures of hexane and methylene chloride ranging from 4:1 to 0:1 as the eluent, to give 10.45 g (yield 65%) of the title sulfide derivative as an oil.

Workup

  1. temperaturewhilst maintaining the internal temperature at between 15° and 20° C
  2. temperaturewas then heated
  3. temperatureunder reflux for 9 hours
  4. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  5. additionThe resulting residue was mixed with diethyl ether and insoluble materials which
  6. filtrationappeared were filtered off
  7. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  8. customthe concentrate was purified by column chromatography through 300 g of silica gel
  9. washa gradient elution method

Sources & evidence

ORD record
ord-de48129b588848eaa6be4102b4b83889
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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