Potassium Carbonate → [5-(2-Methyl-benzothiazol-6-yloxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetic acid ethyl ester

HRID 409293ノート

反応式

HRID 409293 の反応式
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:12]([O:14][C:15](=[O:31])[CH2:16][N:17]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([N+]([O-])=O)[CH:23]=2)[C:18]1=[O:30])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[CH2:12]([O:14][C:15](=[O:31])[CH2:16][N:17]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:11][C:9]3[CH:8]=[CH:7][C:5]4[N:6]=[C:2]([CH3:1])[S:3][C:4]=4[CH:10]=3)[CH:23]=2)[C:18]1=[O:30])[CH3:13]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 7593042-Methyl-1,3-benzothiazol-6-olHCID 784823(5-Nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester

生成物 1

HCID 67110942[5-(2-Methyl-benzothiazol-6-yloxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetic acid ethyl ester収率 42.6%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
105 °C

実験手順

A mixture of 2-methyl-benzothiazol-6-ol (2.30 g, 13.92 mmol), 5-nitro-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester (4.26 g, 15.31 mmol), potassium carbonate (2.3 g, 16.64 mmol) and dimethylacetamide (30 mL) was stirred at 105° C. for twenty hours before it was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo and the residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane to give the title compound as a yellow solid (2.35 g): MS: (+) m/z 397.19 (M+1).

後処理

  1. temperaturewas cooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane

出典と根拠

ORDレコード
ord-3c8457df5c514c929bbe6e2e5e76f01f
出典データセット
uspto-grants-2014_06
特許番号
US08759373B2

反応ノート

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