Acetic Acid → N,N,N'-tricyclohexyl-N'-methoxypropionyl-para-phenylenediamine

HRID 40461Notes

Reaction equation

HRID 40461 reaction equation
[CH:1]1([N:7]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:27]([O:31][CH3:32])(=O)[CH:28]=[CH2:29].C(O)(=[O:35])C>>[CH:21]1([N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8]2[CH:9]=[CH:10][C:11]([N:14]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:29](=[O:35])[CH2:28][CH2:27][O:31][CH3:32])=[CH:12][CH:13]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7294Methyl AcrylateHCID 69058849HCID 69058849, compound

Product 1

HCID 69082158N,N,N'-tricyclohexyl-N'-methoxypropionyl-para-phenylenediamine

Conditions

Temperature
82 °C

Procedure

A 100 ml 3-neck flask was fitted with an overhead stirrer, a thermocouple and a nitrogen inlet. The flask was charged with N,N,N′-tricyclohexyl-para-phenylenediamine (27.1 g), methyl acrylate (150 ml) and glacial acetic acid (10 ml). The reaction was stirred at 82° C. until complete. The reaction mass was taken up in xylenes, extracted with aqueous sodium hydroxide and washed three times with water. Solvent was removed by rotary evaporation. The reaction mass was taken up in hexanes. Some polymer precipitated and was removed. Solvent was removed by rotary evaporation. The product was taken up in xylenes and filtered. Solvent was removed by rotary evaporation. Remaining volatiles were removed by vacuum distillation (29″, 196° C.) to yield a viscous, dark yellow liquid.

Workup

  1. customA 100 ml 3-neck flask was fitted with an overhead stirrer
  2. extractionextracted with aqueous sodium hydroxide
  3. washwashed three times with water
  4. customSolvent was removed by rotary evaporation
  5. customSome polymer precipitated
  6. customwas removed
  7. customSolvent was removed by rotary evaporation
  8. filtrationfiltered
  9. customSolvent was removed by rotary evaporation
  10. customRemaining volatiles were removed by vacuum distillation (29″, 196° C.)
  11. customto yield a viscous, dark yellow liquid

Sources & evidence

ORD record
ord-175e34ccb8e8436d845b25e2912b3ff5
Source dataset
uspto-grants-2013_09
Patent number
US08530397B2

Reaction notes

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