Ethyl Acetate → HCID 67110403, compound

HRID 2077235Notes

Reaction equation

HRID 2077235 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-1f33c9d32335425faf24bb88ce98f685
Source dataset
uspto-grants-2011_04
Patent number
US07928120B2

Reaction notes

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