Hydrochloric Acid → 2-bromo-5-(dimethylsulfamoyl)benzoic Acid

HRID 372237Notes

Reaction equation

HRID 372237 reaction equation
Cl[S:2]([OH:5])(=O)=[O:3].[Br:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:16][NH:17][CH3:18].Cl>O>[Br:6][C:7]1[CH:15]=[CH:14][C:13]([S:2]([N:17]([CH3:18])[CH3:16])(=[O:5])=[O:3])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 69402-Bromobenzoic acidHCID 24638Chlorosulfonic acid

Product 1

HCID 24926932-bromo-5-(dimethylsulfamoyl)benzoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To 160 ml. of chlorosulfonic acid stirring at 0°-5° C. was gradually added 100.5 g. (0.33 mole) of 2-bromobenzoic acid. Stirring was continued as the temperature was allowed to increase to 25° C. The mixture was stirred and refluxed for three hours, then it was cooled and poured into ice-water. The solid was filtered and then washed with cold water until the filtrate was no longer acidic. The solid, thus isolated, was added, in portions, to 200 ml. of a 40% aqueous solution of dimethylamine. After being diluted with 500 ml. of water, the solution was made acidic with 2.5 N hydrochloric acid. Recrystallization of the precipitated solid from aqueous ethanol gave crystals of 2-bromo-5-dimethylaminosulfonylbenzoic acid, m.p. 170°-172° C.

Workup

  1. customat 0°-5° C.
  2. stirringThe mixture was stirred
  3. temperaturerefluxed for three hours
  4. temperatureit was cooled
  5. filtrationThe solid was filtered
  6. washwashed with cold water until the filtrate
  7. customThe solid, thus isolated
  8. additionwas added, in portions, to 200 ml
  9. additionAfter being diluted with 500 ml
  10. customRecrystallization of the precipitated solid from aqueous ethanol

Sources & evidence

ORD record
ord-d828b02245354f65a9c5b42515a07007
Source dataset
uspto-grants-1978_05
Patent number
US04089961

Reaction notes

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