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Water → Methyl benzo[c]isothiazole-4-carboxylate

HRID 1639848
ノート
印刷プレビュー

反応式

HRID 1639848 の反応式
[CH3:1][C:2]1[C:11]([N:12]=[S:13]=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].S(=NS(C)(=O)=O)=O.N1C=CC=CC=1.O>C1C=CC=CC=1>[N:12]1[S:13][CH:1]=[C:2]2[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[CH:10][C:11]=12
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 1049PyridineHCID 10931522Methanesulfonamide, N-sulfinyl-HCID 12255793Methyl 2-methyl-3-(sulfinylamino)benzoate

生成物 1

HCID 12255806Methyl benzo[c]isothiazole-4-carboxylate収率 36.4%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

実験手順

To a solution of methyl 2-methyl-3-(sulfinylamino)benzoate (15.0 g, 71.0 mmol) in benzene (200 mL) was added a solution of N-sulfinylmethanesulfonamide (10.0 g, 71.0 mmol) and pyridine (9.19 mL, 114 mmol) in benzene (80 mL) at 0° C. The reaction mixture was heated under reflux for 18 hr, water was added, and the mixture was extracted with dichloromethane. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80) to give the title compound (5.0 g, yield 36%).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 18 hr
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80)

出典と根拠

ORDレコード
ord-0f6111f19ae042aa8db898a4e83b324b
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08110585B2

反応ノート

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