Sulfuric Acid → 4,6-Dimethyl-benzo[d]isothiazole-3-carboxylic acid methyl ester

HRID 2175178ノート

反応式

HRID 2175178 の反応式
[CH3:1][C:2]1[C:7]2[C:8]([C:11]([OH:13])=[O:12])=[N:9][S:10][C:6]=2[CH:5]=[C:4]([CH3:14])[CH:3]=1.OS(O)(=O)=O.[C:20]([O-])(O)=O.[Na+]>CO>[CH3:20][O:12][C:11]([C:8]1[C:7]2[C:2]([CH3:1])=[CH:3][C:4]([CH3:14])=[CH:5][C:6]=2[S:10][N:9]=1)=[O:13]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 584973864,6-Dimethylbenzo[d]isothiazole-3-carboxylic acid

生成物 1

HCID 584974334,6-Dimethyl-benzo[d]isothiazole-3-carboxylic acid methyl ester収率 94%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of 4,6-dimethyl-benzo[d]isothiazole-3-carboxylic acid (10 mg, 0.048 mmol) in MeOH (5 mL) was added conc. H2SO4 (0.1 mL) at room temperature. The solution was heated up to 60° C. for 24 hours. The solution was cooled and was neutralized with sat. NaHCO3. The solution was extracted with EtOAc. The combined organic layer was dried over MgSO4 and filtered. The filtrate was concentrated and the residue was purified by silica gel flash column chromatography with 20% EtOAc in Hexane as the eluent to afford the title compound (10 mg, 94%) as colorless oil.

後処理

  1. temperatureThe solution was cooled
  2. extractionThe solution was extracted with EtOAc
  3. dry with materialThe combined organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel flash column chromatography with 20% EtOAc in Hexane as the eluent

出典と根拠

ORDレコード
ord-a0ee5fe37ef440cd9ff5f553f978c2cf
出典データセット
uspto-grants-2015_06
特許番号
US09062056B2

反応ノート

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