4-Tert-Butylaniline → HCID 22171936, compound

HRID 1293499Notes

Reaction equation

HRID 1293499 reaction equation
[C:1]1([N:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=O)[CH3:21])[N:15]=2)[CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[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]1([N:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=[N:31][C:30]3[CH:32]=[CH:33][C:27]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:28][CH:29]=3)[CH3:21])[N:15]=2)[CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 698614-Tert-ButylanilineHCID 22171932HCID 22171932, compound

Product 1

HCID 22171936HCID 22171936, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Monoimine (6, 1.25 g, 4.34 mmol) and 4-tert-butylaniline (0.65 g, 4.34 mmol) were dissolved in 50 ml of toluene. To this solution, molecular sieves (4 Å) were added. After standing for 16 hours the mixture was filtered. The solvent was removed in vacuo. The residue was recrystallised from ethanol. Yield 0.44 g (24%) of mixed diimine (7, 96% purity by NMR). H-NMR (CDCl3) δ 8.51 (d, 1H, Py-Hm), 8.38 (d, 1H, Py-Hm), 7.91 (t, 1H, Py-Hp), 7.86 (d, 1H, ArH), 7.78 (d, 1H, ArH), 7.63 (d, 1H, ArH), 7.4-7.6 (m, 5H, ArH), 6.8-6.9 (m, 3H, ArH), 2.43 (s, 3H, Me), 2.37 (s, 3H, Me), 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-ba55f40615e04ce8a74e42c4e83c1684
Source dataset
uspto-grants-2007_07
Patent number
US07238764B2

Reaction notes

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