Hydrochloric Acid → 2-[(4-Butylphenyl)sulfamoyl]benzoic acid

HRID 371353Notes

Reaction equation

HRID 371353 reaction equation
Cl.[CH2:2]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([O:24]C)=[O:23])(=[O:15])=[O:14])=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].[OH-].[Na+]>O>[CH2:2]([C:6]1[CH:7]=[CH:8][C:9]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([OH:24])=[O:23])(=[O:15])=[O:14])=[CH:10][CH:11]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20226978HCID 20226978, compound

Product 1

HCID 155970242-[(4-Butylphenyl)sulfamoyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
85 °C

Procedure

Reaction scheme II is carried out by slowly adding the cooled reaction mixture into a 4 liter beaker containing 250 ml water and 300 ml of hydrochloric acid (37%), and equipped with an efficient stirrer, taking care that the mixture does not foam over. The dispersion is chilled in a refrigerator over night. The crude N-(p-n-butylphenyl)-o-carbomethoxy benzene sulfonamide settles on the bottom of the beaker as a brownish, viscous mass. The water layer is poured off and replaced by a solution of 80 g sodium hydroxide in 1.5 liter of water. The resulting solution is heated for 2 hours at 85° C. to hydrolize the methyl ester (reaction scheme III). ##STR16##

Workup

  1. customReaction scheme II
  2. additionby slowly adding
  3. customthe cooled reaction mixture into a 4 liter beaker
  4. customequipped with an efficient stirrer
  5. temperatureThe dispersion is chilled in a refrigerator over night

Sources & evidence

ORD record
ord-277213f2972041cdac14d2cbd2aba997
Source dataset
uspto-grants-1985_07
Patent number
US04531139

Reaction notes

Loading…