Sodium hydride → HCID 14148378, compound

HRID 247609Notes

Reaction equation

HRID 247609 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]=1[OH:17])([CH3:6])([CH3:5])[CH3:4].[CH2:18]([N:22]1[C:26](=[O:27])[CH:25]=[CH:24][C:23]1=[O:28])[CH2:19][CH2:20][CH3:21]>CS(C)=O>[C:13]([C:9]1[CH:10]=[C:11]([CH:24]2[CH:25]([CH:25]3[CH2:24][C:23](=[O:28])[N:22]([CH2:18][CH2:19][CH2:20][CH3:21])[C:26]3=[O:27])[C:26](=[O:27])[N:22]([CH2:18][CH2:19][CH2:20][CH3:21])[C:23]2=[O:28])[CH:12]=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[C:8]=1[OH:17])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 314052,6-Di-tert-butylphenolHCID 2397801-Butyl-1H-pyrrole-2,5-dione

Product 1

HCID 14148378HCID 14148378, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This compound is prepared by the procedure of Example 1 from 2.40 g (0.1 mol) of sodium hydride, 20.63 (0.1 mol) of 2,6-di-tert-butyl-phenol and 15.31 g (0.1 mol) of N-n-butylmaleimide in dimethyl sulfoxide. The residue is extracted with a 1:1 mixture of hot heptane containing 10 ml of toluene. The heptane extract is concentrated to 150 ml and the resultant solid collected by filtration. The crude product is recrystallized from cyclohexane to give 1.03 g (4%) of a white solid: mp 151°-153° C.

Workup

  1. extractionThe residue is extracted with a 1:1 mixture of hot heptane containing 10 ml of toluene
  2. extractionThe heptane extract
  3. concentrationis concentrated to 150 ml
  4. filtrationthe resultant solid collected by filtration
  5. customThe crude product is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-069542e3c68e4aaf85ffa397b0281918
Source dataset
uspto-grants-1987_11
Patent number
US04709050

Reaction notes

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