Toluene → HCID 21880419, compound

HRID 406900

Reaction equation

HRID 406900 reaction equation
[C:1]1(=[O:11])[N:5]([CH2:6][C:7]([OH:9])=[O:8])[C:4](=[O:10])[CH:3]=[CH:2]1.[C:12]1(C)[CH:17]=[CH:16]C(S(O)(=O)=O)=[CH:14][CH:13]=1.C1(C)C=CC=CC=1.C(O)CCCC>O>[C:4]1(=[O:10])[N:5]([CH2:6][C:7]([O:9][CH2:14][CH2:13][CH2:12][CH2:17][CH3:16])=[O:8])[C:1](=[O:11])[CH:2]=[CH:3]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 62761-PentanolHCID 3199352-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid

Product 1

HCID 21880419HCID 21880419, compoundYield 643.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a separable flask equipped with a Dean-Stark trap, maleimidoacetic acid (reagent grade) (31.0 g, 0.2 mol), p-toluenesulfonic acid (reagent grade) (5.2 g, 0.03 mol), and toluene (reagent grade) (300 ml) were charged. Then, the mixture was stirred and reacted under reduced pressure at 80° C. for 1 hour with dropwise addition of n-pentanol (reagent grade) (17.6 g, 0.2 mol). After the dropwise addition, the mixture was stirred for another 4 hours for allowing the reaction to be continued. During the reaction, the water formed was removed with the Dean-Stark trap. After the reaction, toluene (300 ml) was added and the mixture was washed three times with ion-exchanged water (100 ml). Then, the organic phase obtained was collected and subjected to removal of the toluene by evaporation using an evaporator and a vacuum dryer to give n-pentyl maleimidoacetate (43.5 g). (Yield: ca. 91%. The absence of maleimidoacetic acid and n-pentanol was verified by GPC measurement. The presence of n-pentyl maleimidoacetate was verified by 1H-NMR measurement using DMSO-d6. This compound is referred to hereinafter as Compound A1).

Workup

  1. additionwere charged
  2. additionAfter the dropwise addition
  3. stirringthe mixture was stirred for another 4 hours
  4. customthe reaction
  5. customDuring the reaction
  6. customwas removed with the Dean-Stark trap
  7. customAfter the reaction, toluene (300 ml)
  8. additionwas added
  9. washthe mixture was washed three times with ion-exchanged water (100 ml)
  10. customThen, the organic phase obtained
  11. customwas collected
  12. customsubjected to removal of the toluene by evaporation
  13. customan evaporator

Sources & evidence

ORD record
ord-ac19d27a89eb4590b6786fc66fe0f6b2
Source dataset
uspto-grants-2014_06
Patent number
US08754178B2

Linked notes

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