Ammonium Hydroxide → 5-Chlorothiophene-2-Sulfonamide

HRID 1484457Notes

Reaction equation

HRID 1484457 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[OH-].[NH4+:12]>C(#N)C>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH2:12])(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 27339255-Chlorothiophene-2-sulfonyl chloride

Product 1

HCID 12413015-Chlorothiophene-2-SulfonamideYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

3 g (1 mol equiv.) 5-Chloro-thiophene-2-sulfonyl chloride was dissolved in 30 mL acetonitrile and cooled to 0° C. Dropwise, 6.5 mL (3 mol equiv.) ammoniumhydroxide was added and the reaction mixture was stirred at room temperature for 10 min. Volatiles were removed under reduced pressure, and the solid residue was washed with water and dried in vacuo to afford 2.49 g (91%) 5-chloro-thiophene-2-sulfonic acid amide. 1H NMR (400 MHz, DMSO-d6) δ 7.21 (d, J=4.0 Hz, 1H), 7.43 (d, J=4.0 Hz, 1H), 7.79 (br.s., 2H).

Workup

  1. customVolatiles were removed under reduced pressure
  2. washthe solid residue was washed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-b98b3024bd2e4cef87e677d9f16b9fee
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

Loading…