Sodium Thiosulfate → Benzenesulfonamide, N-[1-(3,5-dichlorobenzoyl)cyclohexyl]-4-methyl-

HRID 2223045Notes

Reaction equation

HRID 2223045 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:27])[C:10]2([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Cl:8])[CH:7]=1)[C:9]([C:10]1([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:27]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 59713392HCID 59713392, compound

Product 1

HCID 10387732Benzenesulfonamide, N-[1-(3,5-dichlorobenzoyl)cyclohexyl]-4-methyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-{1-[(3,5-dichloro-phenyl)-hydroxy-methyl]-cyclohexyl}4-methyl-benzenesulfonamide in CH2Cl2 (4 mL) was added Dess-Martin reagent. The mixture was stirred for 6 hours and saturated aqueous NaHCO3 (5 mL) and solid Na2S2O3 (ca. 1 g) were added. After stirring for 30 min, the mixture was applied to a 10 mL Chem Elut cartridge and allowed to stand for 5 min. The cartridge was eluted with CH2Cl2 (25 mL) and the eluate was evaporated to leave the intended ketone (102 mg) as an oil. The crude product was dissolved in CH2Cl2 (4 mL) and stirred with PS-TsNHNH2 resin (100 mg, 0.28 mmol) for 3 hours. The mixture was filtered and washed with CH2Cl2 (5 mL), ether (5 mL), and CH2Cl2 (5 mL). The filtrate was evaporated to leave N-[1-(3,5-dichloro-benzoyl)-cyclohexyl]4-methyl-benzenesulfonamide (98 mg) as an oil. 1H NMR (500 MHz, CDCl3) δ(ppm): 7.8 (s, 2H), 7.6 (d, 2H), 7.4 (s, 1H), 7.2 (d, 2H), 5.75 (s, 1H), 2.35 (s, 3H), 1.9 (m, 2H), 1.8 (m, 2H), 1.4 (m, 3H), 1.3 (m, 2H), 1.2 (m, 1H).

Workup

  1. stirringAfter stirring for 30 min
  2. waitto stand for 5 min
  3. washThe cartridge was eluted with CH2Cl2 (25 mL)
  4. customthe eluate was evaporated

Sources & evidence

ORD record
ord-87171021fa3c41b49331bcf024d55b5c
Source dataset
uspto-grants-2008_05
Patent number
US07375093B2

Reaction notes

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