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

HRID 1057412Notes

Reaction equation

HRID 1057412 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].[C:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])#[N:17]>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[NH2:17][C:16]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:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

6

Reactant 3

HCID 69132,4,6-TrimethylanilineHCID 7764Ethyl cyanoacetateHCID 8299Hydroxyacetone

Product 1

HCID 18623783HCID 18623783, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 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 (11) 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-5613c7871feb49aeac88b30633132331
Source dataset
uspto-grants-2003_02
Patent number
US06514982B1

Reaction notes

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