Hydrochloric Acid → HCID 11266313, compound

HRID 1838677Notes

Reaction equation

HRID 1838677 reaction equation
Cl[C:2]1[C:10]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:15])[CH:3]=1.[CH3:16][S:17]([O-:19])=[O:18].[Na+].O.Cl>CN(C)C=O>[CH3:16][S:17]([C:2]1[C:10]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:15])[CH:3]=1)(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2733271Sodium methanesulfinate2×HCID 108244784-chloro-2-methyl-5-(methylsulfonyl)Benzoic acid

Product 1

HCID 11266313HCID 11266313, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6 kg of 4-chloro-2-methyl-5-(methylsulfonyl)benzoic acid are dissolved in 15 l of N,N-dimethylformamide (DMF) at room temperature (25°) and subsequently warmed to 50°. 3.6 kg of sodium methanesulfinate are added to this solution. The internal temperature is then raised to 120° and stirred at this temperature for 2 days, with a further 3 kg of sodium methanesulfinate being added after 24 hours. After cooling to 25°, the reaction mixture is introduced into 40 l of water, and 300 g of activated carbon and 1 kg of kieselguhr are added. 5 l of ice are added to the filtrate, and 3.5 l of concentrated hydrochloric acid are added dropwise (pH=1). Recrystallisation from 2-propanol gives 3.8 kg of 4,5-bismethanesulfonyl-2-methylbenzoic acid; m.p. 234-235°.

Workup

  1. temperaturesubsequently warmed to 50°
  2. temperatureThe internal temperature is then raised to 120°
  3. additionadded after 24 hours
  4. temperatureAfter cooling to 25°
  5. additionare added
  6. additionare added dropwise (pH=1)
  7. customRecrystallisation from 2-propanol

Sources & evidence

ORD record
ord-bc5827af3df643b789560eb5634435c3
Source dataset
uspto-grants-2004_01
Patent number
US06673968B1

Reaction notes

Loading…