3,5-Dimethylaniline → HCID 22171931, compound

HRID 1293501Notes

Reaction equation

HRID 1293501 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]=[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=O)[CH3:21])[N:15]=1)[CH3:13])([CH3:4])([CH3:3])[CH3:2].[CH3:23][C:24]1[CH:25]=[C:26]([CH:28]=[C:29]([CH3:31])[CH:30]=1)[NH2:27]>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]=[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=[N:27][C:26]2[CH:28]=[C:29]([CH3:31])[CH:30]=[C:24]([CH3:23])[CH:25]=2)[CH3:21])[N:15]=1)[CH3:13])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 79493,5-DimethylanilineHCID 22171929326613-30-3

Product 1

HCID 22171931HCID 22171931, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Monoimine (9,1.13 g, 3.87 mmol) and 3,5-dimethylaniline (0.5 g, 4.13 mmol) were dissolved in 25 ml of toluene. To this solution, molecular sieves (4 Å) were added. After standing for 60 hours the mixture was filtered. The solvent was removed in vacuo. The residue was recrystallised from ethanol. Yield 0.79 g (52%) of mixed diimine (12). 1H-NMR (CDCl3) δ 8.37 (d, 1H, Py-Hm), 8.32 (d, 1H, Py-Hm), 7.87 (t, 1H, Py-Hp), 7.42 (d, 1H, ArH), 7.18 (t, 1H, ArH), 7.07 (t, 1H, ArH), 6.76 (s, 1H, ArH), 6.54 (d, 1H, ArH), 6.46 (s, 2H, ArH), 2.40 (s, 3H, Me), 2.39 (s, 3H, Me), 2.33 (s, 3H, Me), 1.36 (s, 9H, But).

Workup

  1. additionTo this solution, molecular sieves (4 Å) were added
  2. filtrationthe mixture was filtered
  3. customThe solvent was removed in vacuo
  4. customThe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-c41807551b584518911e8ef505c18b59
Source dataset
uspto-grants-2007_07
Patent number
US07238764B2

Reaction notes

Loading…