4-Tert-Butylaniline → HCID 22171935, compound

HRID 1293500Notes

Reaction equation

HRID 1293500 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].[C:23]([C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24]>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:31][C:30]2[CH:32]=[CH:33][C:27]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:28][CH:29]=2)[CH3:21])[N:15]=1)[CH3:13])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 698614-Tert-ButylanilineHCID 22171929326613-30-3

Product 1

HCID 22171935HCID 22171935, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Monoimine (9,1.06 g, 3.6 mmol) and 4-tert-butylaniline (0.56 g, 3.75 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 0.81 g (53%) of mixed diimine (10). 1H-NMR (CDCl3) δ 8.36 (d, 1H, Py-Hm), 8.34 (d, 1H, Py-Hm), 7.88 (t, 1H, Py-Hp), 7.4 (m, 3H, ArH), 7.18 (t, 1H, ArH), 7.07 (t, 1H, ArH), 6.78 (d, 2H, ArH), 6.54 (d, 1H, ArH), 2.42 (s, 3H, Me), 2.38 (s, 3H, Me), 1.35 (s, 9H, But),1.34 (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-ba93e54128334cffaed67885b0094f54
Source dataset
uspto-grants-2007_07
Patent number
US07238764B2

Reaction notes

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