Ethyl Acetate → HCID 67110403, compound

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

Reactant 4

HCID 8857Ethyl Acetate

HCID 11430Potassium Carbonate

HCID 31374Dimethylacetamide

HCID 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).