Aniline → N-{2-[5-(2-chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]-2-methylpropyl}aniline

HRID 503003Notes

Reaction equation

HRID 503003 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH3:18])[C:10]([C:13]([CH3:17])([CH3:16])[CH:14]=O)=[N:11][N:12]=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH3:18])[C:10]([C:13]([CH3:17])([CH3:16])[CH2:14][NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:11][N:12]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 5049666Sodium triacetoxyborohydrideHCID 866162232-[5-(2-Chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]-2-methylpropanal

Product 1

HCID 68468737N-{2-[5-(2-chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]-2-methylpropyl}aniline

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-[5-(2-Chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]-2-methylpropanal (200 mg) was dissolved in 1,2-dichloroethane (4 ml) and then aniline (73 μl) and sodium triacetoxyborohydride (225 mg) were added thereto, followed by stirring at room temperature for 3 days. The reaction solution was diluted with a saturated aqueous sodium bicarbonate solution (30 ml), followed by extraction with chloroform (10 ml×3). The organic layer was dried and then concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (methanol:chloroform=2:98). The resulting solid washed with diethyl ether to obtain 98 mg of N-{2-[5-(2-chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]-2-methylpropyl}aniline (white solid).

Workup

  1. extractionfollowed by extraction with chloroform (10 ml×3)
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (methanol:chloroform=2:98)
  5. washThe resulting solid washed with diethyl ether

Sources & evidence

ORD record
ord-694dac32ed434df68510d4aa7d3b3120
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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