Ammonium Hydroxide → (1E)-2-Phenylethenesulfonamide

HRID 1484455Notes

Reaction equation

HRID 1484455 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[S:9](Cl)(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[NH4+:14]>C(#N)C>[C:1]1(/[CH:7]=[CH:8]/[S:9]([NH2:14])(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 5369377(E)-2-phenylethene-1-sulfonyl chloride

Product 1

HCID 5357731(1E)-2-PhenylethenesulfonamideYield 38%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

3.3 g (1 mol equiv.) Trans-2-phenyl-ethenesulfonyl chloride was dissolved in 33 mL acetonitrile and cooled to 0° C. Dropwise, 7.7 mL (3 eq) 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 1.13 g (38%) trans-2-phenyl-ethenesulfonic acid amide. 1H NMR (400 MHz, DMSO-d6) δ 7.11 (br.s., 2H), 7.23 (d, J=16.0 Hz, 1H), 7.31 (d, J=16.0 Hz, 1H), 7.41-7.45 (m, 3H), 7.64-7.71 (m, 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-51f978050c6340a0a8939058920f86e7
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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