N-Phenylmaleimide → HCID 14148372, compound

HRID 247614

Reaction equation

HRID 247614 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].[C:18]1([N:24]2[C:28](=[O:29])[CH:27]=[CH:26][C:25]2=[O:30])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1>[C:13]([C:9]1[CH:10]=[C:11]([CH:27]2[CH2:26][C:25](=[O:30])[N:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:28]2=[O:29])[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 13662N-PhenylmaleimideHCID 24758Sodium hydrideHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 14148372HCID 14148372, compoundYield 2.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound is prepared by the procedure of Example 1 from 2.40 g (0.1 mol) of sodium hydride, 20.63 g (0.1 mol) of 2,6-di-tert-butylphenol, and 17.32 g (0.1 mol) of N-phenylmaleimide in tetrahydrofuran. The reaction mixture is concentrated in vacuo and the residue is dissolved in 150 ml of toluene. The toluene solution is extracted sequentially with 1M sodium hydroxide (2×100 ml) and water (2×50 ml). The organic phase is dried over anhydrous sodium sulfate and then the solvent is removed in vacuo. The residue is triturated with petroleum ether to give 0.78 g (2%) of white crystals: mp 204° C.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionthe residue is dissolved in 150 ml of toluene
  3. extractionThe toluene solution is extracted sequentially with 1M sodium hydroxide (2×100 ml) and water (2×50 ml)
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. customthe solvent is removed in vacuo
  6. customThe residue is triturated with petroleum ether

Sources & evidence

ORD record
ord-c2d334ca504d491ba5ca09fb968575eb
Source dataset
uspto-grants-1987_11
Patent number
US04709050

Linked notes

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