Isatoic Anhydride → HCID 3412750, compound

HRID 1947116Notes

Reaction equation

HRID 1947116 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+].I[CH2:16][CH2:17][CH2:18][CH3:19]>CN(C=O)C>[CH2:16]([N:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=2[C:2](=[O:3])[O:4][C:5]1=[O:12])[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 8359Isatoic AnhydrideHCID 10962Butyl iodideHCID 24758Sodium hydride

Product 1

HCID 3412750HCID 3412750, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of isatoic anhydride (8.16 g, 50.0 mmol) in DMF (100 mL) was added sodium hydride (66% in oil, 2.00 g, 55 mmol) under ice-cooling, and the mixture was stirred at the same temperature for 10 min. 1-Iodobutane (8.5 mL, 75 mmol) was added to the obtained mixture and the mixture was stirred at room temperature for 64 hr. Ice water was added to the reaction mixture and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed twice with water and concentrated under reduced pressure to give the title compound (10.5 g), which was used for the next reaction without purification.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 64 hr
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe combined organic layer was washed twice with water
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-87b2fd49b0fb4f2fac74c18e8ea3f18a
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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