Thioanisole → 2-(3-Tert-butyl-4-hydroxylphenyl)-1-(thiazol-2-yl)ethylamine

HRID 1988275Notes

Reaction equation

HRID 1988275 reaction equation
C(OC([NH:11][CH:12]([C:25]1[S:26][CH:27]=[CH:28][N:29]=1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=1)=O)C1C=CC=CC=1.C1(SC)C=CC=CC=1.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl.O>[C:21]([C:16]1[CH:15]=[C:14]([CH2:13][CH:12]([NH2:11])[C:25]2[S:26][CH:27]=[CH:28][N:29]=2)[CH:19]=[CH:18][C:17]=1[OH:20])([CH3:24])([CH3:22])[CH3:23]

Participants

7

Reactant 4

HCID 7520ThioanisoleHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 17819241N-benzyloxycarbonyl-2-(3-tert-butyl-4-hydroxylphenyl)-1-(thiazol-2-yl)ethylamine

Product 1

HCID 178192062-(3-Tert-butyl-4-hydroxylphenyl)-1-(thiazol-2-yl)ethylamineYield 91.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-benzyloxycarbonyl-2-(3-tert-butyl-4-hydroxylphenyl)-1-(thiazol-2-yl)ethylamine (15.28 g, 37.27 mmol) in methylene chloride (1.1 l), thioanisole (8.75 ml, 74.54 mmol) was added. To the mixture, a solution of 1.0M boron tribromide in methylene chloride (186 ml, 186.34 mmol) was added dropwise under cooling with ice and stirred for 1 hour. The reaction mixture was mixed with water and alkalinized by 2N sodium hydroxide and extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure, giving the titled compound (9.46 g, 90%).

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-29cc3805e47945599e2cd1e3bc8ce2ee
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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