Ethyl Acetate → HCID 67110403, compound

HRID 409310Notes

Reaction equation

HRID 409310 reaction equation
[N:1]1([C:7]2[S:8][C:9]3[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18].[C:23](=[O:26])([O-])[O-].[K+].[K+].[CH3:29][C:30]([N:32](C)C)=[O:31]>>[CH2:17]([O:19][C:20](=[O:22])[CH2:21][N:32]1[C:30](=[O:31])[C:29]2[C:12](=[CH:10][CH:9]=[C:15]([O:16][C:14]3[CH:13]=[CH:12][C:10]4[N:11]=[C:7]([N:1]5[CH2:2][CH2:3][O:4][CH2:5][CH2:6]5)[S:8][C:9]=4[CH:15]=3)[CH:14]=2)[C:23]1=[O:26])[CH3:18]

Participants

5

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 6625430HCID 6625430, compound

Product 1

HCID 67110403HCID 67110403, compound

Conditions

Temperature
105 °C

Procedure

A mixture of 2-morpholin-4-yl-benzothiazol-6-ol (238 mg, 1.01 mmol), 5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester (294 mg, 1.06 mmol), potassium carbonate (167 mg, 1.21 mmol) and dimethylacetamide (6 mL) was stirred at 105° C. for twenty-two hours before it was cooled to room temperature and partitioned between chloroform 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 (259 mg): MS: (+) m/z 468.21 (M+1).

Workup

  1. temperaturewas cooled to room temperature
  2. custompartitioned between chloroform 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

Sources & evidence

ORD record
ord-b62990e1bd8b4452a77a6ccc2ef4c925
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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