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

HRID 2223045ノート

反応式

HRID 2223045 の反応式
[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]

参加物

6

反応物 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 59713392HCID 59713392、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-87171021fa3c41b49331bcf024d55b5c
出典データセット
uspto-grants-2008_05
特許番号
US07375093B2

反応ノート

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