Sodium hydride → HCID 22761016, compound

HRID 372630Notes

Reaction equation

HRID 372630 reaction equation
[H-].[Na+].[C:3]([C:6]([NH:12][C:13](=[O:24])[C:14]1[C:15](=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:16](OC)=O)([CH3:11])[C:7]([CH3:10])([CH3:9])[CH3:8])(=[O:5])[NH2:4]>C1(C)C=CC=CC=1>[C:7]([C:6]1([CH3:11])[N:12]2[C:13](=[O:24])[C:14]3[C:15]([C:16]2=[N:4][C:3]1=[O:5])=[CH:20][CH:21]=[CH:22][CH:23]=3)([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 24758Sodium hydride2×HCID 22761009HCID 22761009, compound

Product 1

HCID 22761016HCID 22761016, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of sodium hydride (from 1.92 g of a 50% suspension of sodium hydride in mineral oil) in 150 ml toluene is heated under reflux. During 20 minutes is then added portionwise 6.13 g (0.02 mole) methyl N-(1-carbamoyl-1,2,2-trimethylpropyl)phthalamate to the stirred, refluxing, mixture. Heating is continued for 30 minutes after the addition, the mixture filtered through diatomaceous earth, and the solvent removed in vacuo. The residue crystallizes and is recrystallized from a mixture of acetone-hexane to give 3-t-butyl-3-methyl-5H-imidazo[2,1-a]isoindole-2(3H),5-dione, melting point 136.5°-137.5° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. temperaturerefluxing
  4. temperatureHeating
  5. additionafter the addition
  6. filtrationthe mixture filtered through diatomaceous earth
  7. customthe solvent removed in vacuo
  8. customThe residue crystallizes
  9. customis recrystallized from a mixture of acetone-hexane

Sources & evidence

ORD record
ord-a7af2eca3f974373b2d1ae485926c611
Source dataset
uspto-grants-1978_05
Patent number
US04092147

Reaction notes

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