2-Aminobenzenesulfonamide → HCID 68785778, compound

HRID 2283273Notes

Reaction equation

HRID 2283273 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]=[CH:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]=[CH:20][S:21]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:9])=[O:10])(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 728942-AminobenzenesulfonamideHCID 53662657HCID 53662657, compound

Product 1

HCID 68785778HCID 68785778, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Aminobenzene sulfonamide (153 mg, 0.89 mmol) was added in one portion to a solution of 2-(2-chloro-phenyl)-ethenesulfonyl chloride (150 mg, 0.63 mmol) in pyridine (2 mL) at RT. After 30 minutes of stirring, no more starting material was detected by tlc. The reaction mixture was concentrated under reduced pressure and the residue was taken up in ethyl acetate and a small amount of methanol. The organic phase was washed with 1N HCl, saturated sodium bicarbonate, dried over MgSO4, and concentrated under reduced pressure. Purification by preparative tlc afforded the target compound, which was then recrystallized from ethyl acetate/pentane/diethyl ether to afford the title compound (85 mg, 36%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washThe organic phase was washed with 1N HCl, saturated sodium bicarbonate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by preparative tlc
  6. customafforded the target compound, which
  7. customwas then recrystallized from ethyl acetate/pentane/diethyl ether

Sources & evidence

ORD record
ord-6a4e3d917aae4fe59e3500d047c61601
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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