Isatoic Anhydride → N-(cyclopropylmethyl)isatoic anhydride

HRID 918194Notes

Reaction equation

HRID 918194 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([CH2:18]Br)[CH2:17][CH2:16]1>CC(N(C)C)=O>[CH:15]1([CH2:18][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)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8359Isatoic AnhydrideHCID 24758Sodium hydrideHCID 81503Bromomethylcyclopropane

Product 1

HCID 11672969N-(cyclopropylmethyl)isatoic anhydride

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 20 g. isatoic anhydride in 200 ml. dimethylacetamide is added under nitrogen with stirring sodium hydride obtained from 6 g. of a 57% dispersion in mineral oil, while maintaining the temperature below 25°C. The resulting mixture is stirred at 25°C. for 1 hour and to it is added 17 g. cyclopropylmethylbromide. The mixture is then stirred at room temperature for about 20 hours. It is then poured on water. The mixture is stirred for 15 minutes, the solids collected by filtration, washed with several portions of water and then three times with 0.7 kg. of diethylether. The washed solids are dried to obtain N-(cyclopropylmethyl)isatoic anhydride, m.p. 118°-121°C.

Workup

  1. customobtained from 6 g
  2. temperatureof a 57% dispersion in mineral oil, while maintaining the temperature below 25°C
  3. additionis added 17 g
  4. stirringThe mixture is then stirred at room temperature for about 20 hours
  5. additionIt is then poured on water
  6. stirringThe mixture is stirred for 15 minutes
  7. filtrationthe solids collected by filtration
  8. washwashed with several portions of water
  9. customThe washed solids are dried

Sources & evidence

ORD record
ord-60bd2bfab5144b74ae78554af245c89a
Source dataset
uspto-grants-1976_07
Patent number
US03969506

Reaction notes

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