Trityl chloride → N-triphenylmethylmaleimide

HRID 488056Notes

Reaction equation

HRID 488056 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH:3]=[CH:2]1.[C:8](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:8]([N:5]1[C:4](=[O:6])[CH:3]=[CH:2][C:1]1=[O:7])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 10935Maleimide

Product 1

HCID 301809N-triphenylmethylmaleimideYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Maleimide (20.0 g, 206 mmol) and trityl chloride (57.4 g, 206 mmol) were mixed together in 200 ml of chloroform and triethylamine (31.3, 309 mmol) was added dropwise to the reaction over a period of 20 minutes. After stirring for one hour at room temperature, the reaction was washed with 10% aqueous hydrogen chloride (HCl) solution and dried over magnesium sulfate (MgSO4). The crude product was slurried in 20 ml of ethylacetate. A total of 18.4 g of a solid material was filtered and dried (60% yield). 1H NMR (CDCl3): 7.31 (m, 15H, aromatics), 6.25 (s, 2H, vinyl).

Workup

  1. washthe reaction was washed with 10% aqueous hydrogen chloride (HCl) solution
  2. dry with materialdried over magnesium sulfate (MgSO4)
  3. filtrationA total of 18.4 g of a solid material was filtered
  4. customdried (60% yield)

Sources & evidence

ORD record
ord-afad1fd9329a4c9090efb94c3a8cb72e
Source dataset
uspto-grants-1994_03
Patent number
US05298629

Reaction notes

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