Ethyl Acetate → HCID 67110900, compound

HRID 706248Notes

Reaction equation

HRID 706248 reaction equation
[CH3:1][C:2]1[O: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:17])[CH3:16])[CH3:13].[C:18](=[O:21])([O-])[O-].[K+].[K+].[CH3:24][C:25]([N:27](C)C)=[O:26]>>[CH2:12]([O:14][C:15](=[O:17])[CH2:16][N:27]1[C:25](=[O:26])[C:24]2[C:7](=[CH:5][CH:4]=[C:10]([O:11][C:9]3[CH:8]=[CH:7][C:5]4[N:6]=[C:2]([CH3:1])[O:3][C:4]=4[CH:10]=3)[CH:9]=2)[C:18]1=[O:21])[CH3:13]

Participants

5

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 6765042-Methyl-1,3-benzoxazol-6-ol

Product 1

HCID 67110900HCID 67110900, compound

Conditions

Temperature
105 °C

Procedure

A mixture of 2-methyl-benzooxazol-6-ol (8.41 g, 56 mmol), 5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester (17.23 g, 62 mmol), potassium carbonate (9.36 g, 67.7 mmol), and dimethylacetamide (120 mL) was stirred at 105° C. for twenty 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 (9.18 g): MS: (+) m/z 381.27 (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-ef165d42dc0744aca5e473f434441150
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

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