Hydrochloric Acid → N-{3-[2-(4-Cyanophenyl)ethylthio]phenyl}benzenesulfonamide

HRID 325042Notes

Reaction equation

HRID 325042 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[CH:13]=1.Cl>N1C=CC=CC=1.C(Cl)Cl>[C:27]([C:24]1[CH:25]=[CH:26][C:21]([CH2:20][CH2:19][S:18][C:14]2[CH:13]=[C:12]([NH:11][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[CH:17]=[CH:16][CH:15]=2)=[CH:22][CH:23]=1)#[N:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 22033546Amino-3-[2-(4-cyanophenyl)ethylthio]benzene

Product 1

HCID 22033483N-{3-[2-(4-Cyanophenyl)ethylthio]phenyl}benzenesulfonamideYield 82.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (0.62 g; 3.5 mmol) was added to a cold solution (ice:water temperature) of amino-3-[2-(4-cyanophenyl)ethylthio]benzene (0.80 g; 3.15 mmol; from step (ii) above) in a mixture of pyridine (1 mL) and CH2Cl2 (20 mL) over 10 minutes. After 3 hours stirring, 2M aqueous HCl was added and the solution extracted with CH2Cl2. The organic layer was dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography (SiO2; Et2O:hexane (1:1)) to give 1.02 g (82%) of the sub-title compound.

Workup

  1. extractionthe solution extracted with CH2Cl2
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by flash chromatography (SiO2; Et2O:hexane (1:1))

Sources & evidence

ORD record
ord-faba57997a054bab80312058841c4918
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

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