Potassium Hydroxide → 5-(4-Carboxymethylphenylthio)thiophene-2-sulfonamide

HRID 231679

Reaction equation

HRID 231679 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[OH-].[K+].Br[C:15]1[S:19][C:18]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:17][CH:16]=1>CN(C)C=O.O>[C:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([S:1][C:15]2[S:19][C:18]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:17][CH:16]=2)=[CH:7][CH:6]=1)([OH:11])=[O:10]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 12413045-Bromo-2-thiophenesulfonamideHCID 33905114-Mercaptophenylacetic acid

Product 1

HCID 200336935-(4-Carboxymethylphenylthio)thiophene-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

4-Mercaptophenylacetic acid (2.3 g) was dissolved in dimethylformamide under a nitrogen atmosphere and 1.8 g of potassium hydroxide dissolved in a minimum amount of water was added. 5-bromothiophene-2-sulfonamide (3.3 g) dissolved in dimethylformamide was added and the mixture heated at 120° C. for 2 hours. After cooling to room temperature water was added to the reaction mixture, the pH was adjusted to 8.6 and the mixture was extracted with ethyl acetate. The aqueous phase was separated and acidified, causing a solid to precipitate. The solid was collected by filtration and dried under vacuum to a weight of 3.25 g.

Workup

  1. additionwas added
  2. additionwas added
  3. additionwas added to the reaction mixture
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe aqueous phase was separated
  6. customto precipitate
  7. filtrationThe solid was collected by filtration
  8. customdried under vacuum to a weight of 3.25 g

Sources & evidence

ORD record
ord-e9ec0aeb8d5c4266906869950d3ea639
Source dataset
uspto-grants-1989_07
Patent number
US04847289

Linked notes

Loading…