Formaldehyde → Succinimide, N-(p-phenetidinomethyl)-

HRID 1876195Notes

Reaction equation

HRID 1876195 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH3:11])=[CH:6][CH:5]=1)[CH3:2].C(OC1C=CC(N)=CC=1)C.[C:22]1(=[O:28])[NH:26][C:25](=[O:27])[CH2:24][CH2:23]1.C=O>CCO>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][N:26]2[C:22](=[O:28])[CH2:23][CH2:24][C:25]2=[O:27])=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 90764-EthoxyanilineHCID 11439SuccinimideHCID 5790224-ethoxy-N-methylaniline

Product 1

HCID 142255Succinimide, N-(p-phenetidinomethyl)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(4-Ethoxy-phenyl)-methyl-amine: A mixture of 2 g (14.57 mmol) of 4-ethoxy-phenylamine, 1.73 g (17.49 mmol) of succinimide, and 1.4 mL (17.49 mmol) of 37% aq formaldehyde in 15 mL of EtOH was heated at reflux for 18 hours. The reaction mixture cooled down and precipitate was filtered and washed with Et2O, dried to give 2.89 g (11.27 mmol) of 1-[(4-ethoxy-phenylamino)-methyl]-pyrrolidine-2,5-dione, which was dissolved in DMSO and treated with 0.428 g (11.27 mmol) of NaBH4. The reaction mixture was heated in a hot water bath for 15 min, then it was poured into 20 mL of cold water and extracted with Et2O (3×15 mL), the organic extracts were combined and concentrated to give 1.7 g of the title compound. LC-MS (ESI+; 152 ([M+H]+)).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe reaction mixture cooled down
  4. customprecipitate
  5. filtrationwas filtered
  6. washwashed with Et2O
  7. customdried

Sources & evidence

ORD record
ord-9b9bbf65aef74a9b837792485084e74d
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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