Hydrochloric Acid → [2-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)benzyl]amine

HRID 1351694Notes

Reaction equation

HRID 1351694 reaction equation
CC(S([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([C:18]1[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)(=[O:17])=[O:16])=O)(C)C.Cl>CO.O1CCOCC1>[F:32][C:29]1[CH:28]=[CH:27][C:26](/[CH:25]=[CH:24]/[C:21]2[CH:22]=[CH:23][C:18]([S:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][NH2:7])(=[O:17])=[O:16])=[CH:19][CH:20]=2)=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21099479HCID 21099479, compound

Product 1

HCID 21099441[2-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)benzyl]amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Methyl-N-[2-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)benzyl]propane-2-sulfinamide (Example 177, 285 mg, 0.6 mmol) was dissolved in methanol (5 mL) and 4N HCl in dioxane (5 mL) and stirred overnight at room temperature. The solvent was removed in vacuo and the residue triturated with diethyl ether to give the title compound as the hydrochloride salt (221 mg, 90%). δH (500 MHz, d6 DMSO): 8.46–8.38 (3H, m), 8.13 (1H, d, J=7.8 Hz), 7.89 (2H, d, J=8.3 Hz), 7.84–7.78 (3H, m), 7.71–7.67 (4H, m), 7.45 (1H, d, J=16.5 Hz), 7.30 (1H, d, J=16.5 Hz), 7.23 (2H, t, J=8.7 Hz), 4.28 (2H, s).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-0f4e0d8e6c094fdba9fbdc035dfd7631
Source dataset
uspto-grants-2007_05
Patent number
US07217740B2

Reaction notes

Loading…