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

HRID 409293

Reaction equation

[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]

Participants

Conditions

Temperature: 105 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-3c8457df5c514c929bbe6e2e5e76f01f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759373B2

Linked notes

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