Isatoic Anhydride → HCID 9856484, compound

HRID 1743740Notes

Reaction equation

HRID 1743740 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3].[H-].[Na+].[CH:15]1([CH2:21]Br)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(OCC)(=O)C>CN(C)C(=O)C.O>[CH:15]1([CH2:21][N:6]2[C:5](=[O:12])[O:4][C:2](=[O:3])[C:1]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:7]23)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 8359Isatoic AnhydrideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 9856484HCID 9856484, compoundYield 23.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

815 mg (5 mmol) of isatoic acid anhydride is dissolved in 15 ml of N,N-dimethylacetamide and mixed under cover gas and in a moisture-free environment with 220 mg (5.5 mmol) of sodium hydride (60% dispersion in mineral oil). It is heated for 1 hour to 60° C. After cooling, 885 mg (5 mmol) of cyclohexylmethyl bromide is added, and the batch is heated to 60° C. for 4 hours. It is then diluted with water to 60 ml and shaken out three times with ethyl acetate. The combined organic phase is washed with water, dried, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with hexane:ethyl acetate=1:1 as an eluant. 300 mg of N-cyclohexylmethylisatoic acid anhydride is obtained.

Workup

  1. temperatureIt is heated for 1 hour to 60° C
  2. temperatureAfter cooling
  3. washThe combined organic phase is washed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe residue is chromatographed on silica gel with hexane

Sources & evidence

ORD record
ord-429481f4452e47fcb5b93c1fc6f8d9c8
Source dataset
uspto-grants-2006_03
Patent number
US07012081B2

Reaction notes

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