Benzoic acid, 2-((2,6-dichloro-3-methylphenyl)amino)-, methyl ester → 1-[2-[(2,6-Dichloro-3-methylphenyl)amino]phenyl]-2-(methylsulfinyl)ethanone

HRID 1461431Notes

Reaction equation

HRID 1461431 reaction equation
CO[C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([CH3:18])[C:12]=1[Cl:19].[CH3:21][S:22]([CH3:24])=[O:23].C1COCC1>C1COCC1>[Cl:19][C:12]1[C:13]([CH3:18])=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[NH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3](=[O:20])[CH2:21][S:22]([CH3:24])=[O:23]

Participants

4

Reactant 2

HCID 76743Benzoic acid, 2-((2,6-dichloro-3-methylphenyl)amino)-, methyl esterHCID 21830753dimethylsulfoxide THF

Product 1

HCID 150273821-[2-[(2,6-Dichloro-3-methylphenyl)amino]phenyl]-2-(methylsulfinyl)ethanoneYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[(2,6-Dichloro-3-methylphenyl)amino]benzoic acid methyl ester (3.3 g, 10.6 mmol) is dissolved in 30 ml of dry THF and added to a solution of dimsyl anion (JACS, 84, 866, 1982) (31.9 mmol) in 60 ml of 1:1 DMSO/THF at 0° C. under argon. When addition is complete, the ice bath is removed and the reaction mixture is stirred at room temperature for five hours. The reaction is quenched with 400 ml of 1N hydrochloric acid, and extracted twice with 300 ml of chloroform. The combined chloroform extract is washed with 300 ml of water three times, and once with 300 ml of brine. This chloroform layer is dried over magnesium sulfate and evaporated. The residue solidifies after being dried at room temperature under vacuum for 12 hours. Recrystallization from methylene chloride in hexane gives 1.0 g of 1-[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]-2-(methylsulfinyl)ethanone (26% yield); mp 152°-154° C.

Workup

  1. additionWhen addition
  2. customthe ice bath is removed
  3. customThe reaction is quenched with 400 ml of 1N hydrochloric acid
  4. extractionextracted twice with 300 ml of chloroform
  5. extractionThe combined chloroform extract
  6. washis washed with 300 ml of water three times
  7. dry with materialThis chloroform layer is dried over magnesium sulfate
  8. customevaporated
  9. customafter being dried at room temperature under vacuum for 12 hours
  10. customRecrystallization from methylene chloride in hexane

Sources & evidence

ORD record
ord-2e75e642d38a4588a50924fb9c58f45b
Source dataset
uspto-grants-1991_12
Patent number
US05075330

Reaction notes

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