p-Toluidine → HCID 178426386, compound

HRID 603920Notes

Reaction equation

HRID 603920 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:5][CH:4]=1)=O.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[CH3:25][C:22]1[CH:23]=[CH:24][C:19](/[N:18]=[CH:1]/[C:3]2[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:5][CH:4]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 7813p-ToluidineHCID 639902Tert-butyl 2-(4-formylphenoxy)acetate

Product 1

HCID 178426386HCID 178426386, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl (4-formylphenoxy)acetate (5.0 g, 21.2 mmol) was dissolved in dry toluene (100 mL) and p-toluidine (2.27 g, 21.2 mmol) was added. The mixture was refluxed in a Dean-Stark apparatus for 18 hours, cooled and concentrated under reduced pressure. Heptane was added and the mixture was concentrated under reduced pressure. This afforded the title compound.

Workup

  1. temperatureThe mixture was refluxed in a Dean-Stark apparatus for 18 hours
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. additionHeptane was added
  5. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7e08c27e3a1548faaee68adffb568624
Source dataset
uspto-grants-2011_03
Patent number
US07906502B2

Reaction notes

Loading…