Toluene → 2-Phenylthiomethyl-4-sec-butyl-6-methoxysaccharin

HRID 129053ノート

反応式

HRID 129053 の反応式
[CH:1]([C:5]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]2[C:6]=1[C:7](=[O:18])[NH:8][S:9]2(=[O:11])=[O:10])([CH2:3][CH3:4])[CH3:2].CC(C)([O-])C.[K+].C1([CH:31]([S:33]C(Cl)C2C=CC=CC=2)Cl)C=CC=CC=1.[C:42]1(C)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:42]1([S:33][CH2:31][N:8]2[C:7](=[O:18])[C:6]3[C:12](=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:5]=3[CH:1]([CH2:3][CH3:4])[CH3:2])[S:9]2(=[O:10])=[O:11])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

参加物

6

反応物 4

HCID 1140TolueneHCID 20138743Phenylchloromethyl sulfideHCID 23665647Potassium tert-butoxideHCID 677845614-Sec-butyl-6-methoxysaccharin

生成物 1

HCID 677843062-Phenylthiomethyl-4-sec-butyl-6-methoxysaccharin収率 60%

試薬・触媒・溶媒 1

HCID 74236Tetrabutylammonium Bromide触媒

実験手順

A mixture of 4-sec-butyl-6-methoxysaccharin (3 g), toluene, potassium t-butoxide (1.4 g), and tetrabutylammonium bromide (0.4 g) was brought to reflux and phenylchloromethyl sulfide (1.8 mL) was added. The reaction mixture was refluxed for about 27 hours, the solvent was removed in vacuo, the residue was extracted with ethyl acetate, washed with brine and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by column chromatography on silica eluting with 10% ethyl acetate/hexane to afford 2.63 g (60%) of 2-phenylthiomethyl-4-sec-butyl-6-methoxysaccharin.

後処理

  1. temperatureto reflux
  2. temperatureThe reaction mixture was refluxed for about 27 hours
  3. customthe solvent was removed in vacuo
  4. extractionthe residue was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by column chromatography on silica eluting with 10% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-84f738588e9e4ac995771c12a62e54f0
出典データセット
uspto-grants-1995_11
特許番号
US05466701

反応ノート

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