2,4,6-Trimethylaniline → HCID 18623783, compound

HRID 1860437Notes

Reaction equation

HRID 1860437 reaction equation
[CH3:1][C:2]([CH2:4]O)=O.[CH3:6][C:7]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:8]=1[NH2:9].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:28]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])#[N:29]>C1C=CC=CC=1>[NH2:29][C:28]1[N:9]([C:8]2[C:10]([CH3:15])=[CH:11][C:12]([CH3:14])=[CH:13][C:7]=2[CH3:6])[C:2]([CH3:4])=[CH:1][C:30]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

6

Reactant 4

HCID 69132,4,6-TrimethylanilineHCID 7764Ethyl cyanoacetateHCID 8299HydroxyacetoneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 18623783HCID 18623783, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of acetol (1′) (20 mL, 0.26 mol), 2,4,6-trimethylaniline (2′) (36.5 mL, 0.260 mol), and 4-toluenesulfonic acid monohydrate (0.21 g) were refluxed in benzene (115 mL) using a Dean-Stark trap to remove water. After 2 hours, ethyl cyanoacetate (27.7 mL, 0.26 mol) was added and heating was continued for 14 hours. The mixture was cooled to room temperature, concentrated, and the residue chromatographed (elution with 15% ethyl acetate in hexanes) to afford 21.4 g (29%) of compound (3′) as a yellow oil.

Workup

  1. customto remove water
  2. temperatureheating
  3. waitwas continued for 14 hours
  4. concentrationconcentrated
  5. customthe residue chromatographed
  6. wash(elution with 15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5a69d0085f8a46678caaf3e14e968263
Source dataset
uspto-grants-2003_03
Patent number
US06531475B1

Reaction notes

Loading…