Pyridine → 2-Ethylcarbonate Ethylmaleimide

HRID 23966Notes

Reaction equation

HRID 23966 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:5]([NH:7][C:8](=[O:10])[CH:9]=1)=[O:6].N1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1>[CH2:3]([C:4]1[C:5]([NH:7][C:8](=[O:10])[CH:9]=1)=[O:6])[CH3:2].[CH3:22][CH2:21][O:20][C:18](=[O:1])[OH:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 22337974Hydroxy ethylmaleimide

Product 1

HCID 685376102-Ethylcarbonate Ethylmaleimide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydroxy ethylmaleimide (29.87 g, 0.212 moles) and pyridine (16.7 g, 0.212 moles) were dissolved in THF (170 mL) and the solution was stirred at room temperature. Ethyl chloroformate (22.97 g, 0.212 moles) was added dropwise and stirred for 90 minutes. The pyridine salt was filtered off and the solution was combined with 200 mL of a 1N HCl solution. The product was extracted with methylene chloride and washed with a 1N HCl solution followed by water and then dried over magnesium sulfate. The red solution was concentrated and the red crystals purified by sublimation yielding white crystals, m.p. 52° C. (34.76 g, 77.04%). 1H-NMR (CDCl3), δ, ppm): 1.26-1.34 (3H, —CH3, t), 3.81-3.87 (2H —NCH2—, t), 4.14-4.25 (2H, δ-CH2OC═O, q), 4.25-4.30 (2H, β-CH2O—, t), 6.74 (2H, —CH═CH—, s). 13C-NMR (CDCl3, δ, ppm): 14.2 (1C, —CH3), 36.8 (1C, —NCH2—), 64.3 (1C, δ-CH2O), 64.5 (1C, β-CH2—), 134.4 (2C, —CH═CH—), 154.9 (1C, O(C═O)O), 170.4 (2C, —C═O).

Workup

  1. stirringstirred for 90 minutes
  2. filtrationThe pyridine salt was filtered off
  3. extractionThe product was extracted with methylene chloride
  4. washwashed with a 1N HCl solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe red solution was concentrated
  7. customthe red crystals purified by sublimation
  8. customyielding white crystals, m.p. 52° C. (34.76 g, 77.04%)

Sources & evidence

ORD record
ord-be361221d8954c20ad0e2af6c64cbc63
Source dataset
uspto-grants-2005_02
Patent number
US06855745B2

Reaction notes

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