Hydrochloric Acid → 3-methylthio-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one

HRID 840980ノート

反応式

HRID 840980 の反応式
S([O-])([O-])=O.[Na+].[Na+].N[C:8]1[CH:19]=[CH:18][C:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[C:10]=2[CH:9]=1.Cl.O.O.O.C([O-])(=O)C.[Na+].[CH3:29][S-:30].[Na+].[OH-].[Na+]>O>[CH3:29][S:30][C:8]1[CH:19]=[CH:18][C:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[C:10]=2[CH:9]=1

参加物

8

反応物 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 2668073-amino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-oneHCID 4378561Sodium methanethiolateHCID 23665404Sodium Acetate Trihydrate

生成物 1

HCID 226205033-methylthio-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one収率 46%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of sodium sulfite (3.31 g, 47.94 mmol) in water (5 ml) was added dropwise to a mixture of 3-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (8.00 g, 45.65 mmol) and 35% hydrochloric acid (20 ml) under ice-cooling and stirred under ice-cooling for 20 minutes. Sodium acetate trihydrate (33 g) was added to the reaction mixture and the resulting mixture was added dropwise to a 15% aqueous sodium thiomethoxide solution (42.67 g, 91.31 mmol). The reaction mixture was stirred at 80° C. for 1.5 hours, adjusted to pH 9 with an aqueous sodium hydroxide solution and then extracted with ethyl acetate. The extract solution was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/30) to obtain 4.33 g of 3-methylthio-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one.

後処理

  1. temperaturecooling
  2. temperaturecooling for 20 minutes
  3. stirringThe reaction mixture was stirred at 80° C. for 1.5 hours
  4. extractionextracted with ethyl acetate
  5. washThe extract solution was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/30)

出典と根拠

ORDレコード
ord-7d4000496e0c473ab6affa1d0ce2216d
出典データセット
uspto-grants-2002_04
特許番号
US06369110B1

反応ノート

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