p-Toluenesulfonic acid → HCID 15555425, compound

HRID 1692523Notes

Reaction equation

HRID 1692523 reaction equation
C[C:2]([CH3:8])([CH2:5][NH:6][CH3:7])[CH:3]=O.[C:9](OC(=O)C)(=[O:11])[CH3:10].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:27]([O-:30])([O-])=O.[Na+].[Na+]>O>[CH3:8][C:2]([CH3:3])([CH:27]=[O:30])[CH2:5][N:6]([CH3:7])[C:9](=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 15555432HCID 15555432, compound

Product 1

HCID 15555425HCID 15555425, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a round-bottom flask with a mounted reflux condenser and under nitrogen atmosphere, 20.0 g (0.17 mol) of 2,2-dimethyl-3-methylamino-propanal was introduced while being stirred. 30.0 g (0.52 mol) of acetic acid anhydride was slowly added in drops to this, the mixture was mixed wtih 0.1 g of para-toluenesulfonic acid, and it was heated for 1 hour to 120° C. After cooling to room temperature, the reaction mixture was mixed with 100 ml of water, neutralized with Na2CO3, extracted several times with ethyl acetate, and the combined organic phase was dried on MgSO4 and concentrated by evaporation. The thus obtained brown oil was fractionated in a vacuum. The product distilled at an overhead temperature of 93-95° C. and a pressure of 3 mbar. Yield: 8.2 g (30% of theory) of colorless and almost odorless liquid, which crystallized when left to stand.

Workup

  1. temperatureIn a round-bottom flask with a mounted reflux condenser
  2. temperaturewas heated for 1 hour to 120° C
  3. extractionextracted several times with ethyl acetate
  4. customthe combined organic phase was dried on MgSO4
  5. concentrationconcentrated by evaporation
  6. distillationThe product distilled at an overhead temperature of 93-95° C.
  7. customYield: 8.2 g (30% of theory) of colorless and almost odorless liquid, which crystallized when
  8. waitleft

Sources & evidence

ORD record
ord-eedcbac7d0fb486ea775da2f371ad3fb
Source dataset
uspto-grants-2012_04
Patent number
US08157950B2

Reaction notes

Loading…