Tert-Butylamine → 2-(4-Amino-3-chloro-5-trifluoromethylphenyl)-2-tert-butylaminoethanol

HRID 11899

Reaction equation

HRID 11899 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([CH:12]2[O:14][CH2:13]2)=[CH:4][C:3]=1[Cl:15].[C:16]([NH2:20])([CH3:19])([CH3:18])[CH3:17]>C(O)C>[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([CH:12]([NH:20][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:13][OH:14])=[CH:4][C:3]=1[Cl:15]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 15067147(4-Amino-3-chloro-5-trifluoromethyl-phenyl)-ethylene oxide

Product 1

HCID 99977892-(4-Amino-3-chloro-5-trifluoromethylphenyl)-2-tert-butylaminoethanolYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.2 g (0.022 mol) of (4-amino-3-chloro-5-trifluoromethyl-phenyl)-ethylene oxide was dissolved in 26 ml of anhydrous ethanol and treated with 5.1 ml (0.049 mol) of tert-butylamine. The mixture was refluxed for 13 h, and then evaporated. The residue was extracted with 2N hydrochloric acid for several times. Aqueous layers were combined and extracted with toluene and treated with activated carbon. The pH was adjusted to 10 with 20% sodium hydroxide solution. The precipitate was collected by filtration, 2-(4-amino-3-chloro-5-trifluoromethylphenyl)-2-tert-butylaminoethanol was obtained. Yield 20–30%; melting point 85–90° C.

Workup

  1. temperatureThe mixture was refluxed for 13 h
  2. customevaporated
  3. extractionThe residue was extracted with 2N hydrochloric acid for several times
  4. extractionextracted with toluene
  5. additiontreated with activated carbon
  6. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-5946892308ac4131bb6fd116f5fb02cd
Source dataset
uspto-grants-2006_08
Patent number
US07098364B2

Linked notes

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