Hydrochloric Acid → N-[[(4-chlorophenyl)amino]carbonyl]-5-methoxy-2-thiophenesulfonamide

HRID 1464123Notes

Reaction equation

HRID 1464123 reaction equation
[CH3:1][O:2][C:3]1[S:7][C:6]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:5][CH:4]=1.[OH-].[Na+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[O:23])=[CH:17][CH:16]=1.Cl>CC(C)=O>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:11][S:8]([C:6]2[S:7][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:10])=[O:9])=[O:23])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76934-Chlorophenyl IsocyanateHCID 14798Sodium HydroxideHCID 15669309HCID 15669309, compound

Product 1

HCID 9884635N-[[(4-chlorophenyl)amino]carbonyl]-5-methoxy-2-thiophenesulfonamideYield 61.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 5-methoxy-2-thiophenesulfonamide (7.6 g, 39.4 mmole) in 23 ml of acetone was added aqueous sodium hydroxide (46 ml of 1N, 46 mmole) followed by a solution of 4-chlorophenyl isocyanate (7.91 g, 51.3 mmole) dissolved in 23 ml of acetone. This mixture was stirred at room temperature for 18 hrs. and filtered. The filtrate was acidified with hydrochloric acid (47.5 ml of 1N, 47.5 mmole) and stirred vigorously for 30 min. The resultant precipitate was filtered and washed with water The material was slurried with a minimal amount of ethanol and filtered to produce 8.4 g of a colorless solid.

Workup

  1. filtrationand filtered
  2. stirringstirred vigorously for 30 min
  3. filtrationThe resultant precipitate was filtered
  4. washwashed with water The material
  5. filtrationfiltered

Sources & evidence

ORD record
ord-51a07e10fb0a481fb62023a841c81ea5
Source dataset
uspto-grants-1994_04
Patent number
US05302724

Reaction notes

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