Acetic Acid → HCID 69456164, compound

HRID 1268886Notes

Reaction equation

HRID 1268886 reaction equation
[C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]([N:10]([CH2:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17])[CH2:11][CH3:12])[CH3:9].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:8]([N:10]([CH2:13][C:14]1[CH:15]=[C:16]([NH:17][C:1]([CH3:2])=[CH:4][C:5](=[O:7])[CH3:6])[CH:18]=[CH:19][CH:20]=1)[CH2:11][CH3:12])[CH3:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acid2×HCID 31261Acetylacetone3×HCID 3359246(3-Aminobenzyl)diethylamine2×

Product 1

HCID 69456164HCID 69456164, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.00 g (9.99 mmol) Acetylacetone, 1.78 g (9.99 mmol) 3-[(diethylamino)methyl]-aniline, and 0.15 g (2.5 mmol) 4-toluenesulfonic acid are dissolved in 100 ml toluene. The reaction mixture is refluxed overnight with a Dean-Stark trap to remove water. 0.05 g (0.83 mmol) 4-toluenesulfonic acid are again added and the mixture is refluxed overnight. As tlc control showed that there is some 3-[(diethylamino)-methyl]aniline left, 0.2 g (2 mmol) acetylacetone are added and refluxing is continued for 4 h. To drive the reaction to completion, 0.6 ml (9.98 mmol) acetic acid and 0.2 g (2 mmol) acetylacetone are added and the mixture is refluxed overnight with a Dean-Stark trap. After cooling down to room temperature, the solvent is removed in vacuo and the residue is purified by column chromatography on silica with dichloromethane/methanol mixtures as eluent.

Workup

  1. temperatureThe reaction mixture is refluxed overnight with a Dean-Stark trap
  2. customto remove water
  3. temperaturethe mixture is refluxed overnight
  4. waitleft
  5. temperaturerefluxing
  6. additionare added
  7. temperaturethe mixture is refluxed overnight with a Dean-Stark trap
  8. customthe solvent is removed in vacuo
  9. customthe residue is purified by column chromatography on silica with dichloromethane/methanol

Sources & evidence

ORD record
ord-f56795cd69494eab86f45a0d8cac3ce2
Source dataset
uspto-grants-2007_04
Patent number
US07199136B2

Reaction notes

Loading…