Water → 2,4-Dichloro-6-(4,5-dihydro-1H-imidazol-2-yl)benzenamine

HRID 2052800

Reaction equation

HRID 2052800 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].C([Li])CCC.[Cl:10][C:11]1[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([C:19](F)(F)F)[C:12]=1[NH2:13].O>C(OCC)C>[Cl:10][C:11]1[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([C:19]2[NH:3][CH2:2][CH2:1][N:4]=2)[C:12]=1[NH2:13]

Participants

6

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 12682552,4-Dichloro-6-(trifluoromethyl)anilineHCID 178418339Butyllithium

Product 1

HCID 118170722,4-Dichloro-6-(4,5-dihydro-1H-imidazol-2-yl)benzenamineYield 36.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of ethylene diamine (1.2 mL, 18 mmol) in ethyl ether (50 mL) at −20° C. was added n-butyl lithium (6.4 mL, 2.5 M in hexanes, 16 mmol). The mixture was stirred at 0° C. for 0.3 hour before the addition of 2,4-dichloro-6-trifluoromethyl aniline (0.92 g, 4.2 mmol). The mixture was stirred at 0° C. for an additional 1.5 hours, at which point water (0.36 mL, 20 mmol) was added and the solvent was removed under reduced pressure. Purification by flash column chromatography (silica gel, 1% to 10% methanol in dichloromethane) to give the title compound of Step A (0.35 g) as a yellow solid.

Workup

  1. additionwas added
  2. customthe solvent was removed under reduced pressure
  3. customPurification by flash column chromatography (silica gel, 1% to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-108abbfac5ef4efa9ff9a1344a16d7e8
Source dataset
uspto-grants-2008_02
Patent number
US07326704B2

Linked notes

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