N-Methylaniline → HCID 71183837, compound

HRID 1848399Notes

Reaction equation

HRID 1848399 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([O:13][CH2:14][CH:15]([CH2:21][O:22][C:23](=[O:26])[CH:24]=[CH2:25])[O:16][C:17](=[O:20])[CH:18]=[CH2:19])(=[O:12])[CH:10]=[CH2:11]>C(O)(=O)C>[CH3:1][N:2]([CH2:11][CH2:10][C:9]([O:13][CH2:14][CH:15]([O:16][C:17](=[O:20])[CH2:18][CH2:19][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH2:21][O:22][C:23](=[O:26])[CH2:24][CH2:25][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 79569Propane-1,2,3-triyl triprop-2-enoate

Product 1

HCID 71183837HCID 71183837, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Propoxylated glycerol triacrylate (GPTA—OTA 480, 5.08 g) was added to N-methylaniline (6.42 g—an equivalent amount required to react with the three acrylate groups, had the reactant been glycerol triacrylate) in glacial acetic acid (10 ml). The reaction mixture was heated at 100° C. for 2 hours and then the acetic acid removed by vacuum distillation. A portion of the residue (11 g) was then subjected to steam distillation to remove the excess N-methylaniline and the product extracted with dichloromethane (25 ml). The extract was dried over anhydrous magnesium sulphate, filtered and the dichloromethane removed by distillation in vacuo to leave a pale brown-coloured oil (6.46 g).

Workup

  1. customto react with the three acrylate groups
  2. customthe acetic acid removed by vacuum distillation
  3. distillationA portion of the residue (11 g) was then subjected to steam distillation
  4. customto remove the excess N-methylaniline
  5. extractionthe product extracted with dichloromethane (25 ml)
  6. dry with materialThe extract was dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customthe dichloromethane removed by distillation in vacuo

Sources & evidence

ORD record
ord-84a710e1ea64465e9d55a1c601eef23f
Source dataset
uspto-grants-2015_02
Patent number
US08952190B2

Reaction notes

Loading…