Sodium → (3-Fluoro-benzyl)-[2-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-ethyl]-amine

HRID 8637

Reaction equation

HRID 8637 reaction equation
[Na].[O:2]1[C:6]2[CH:7]=[CH:8][S:9][C:5]=2[C:4]([C:10]2[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=2)=[N:3]1.Br[CH2:18][CH2:19][NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1>C1(C)C=CC=CC=1>[F:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][NH:20][CH2:19][CH2:18][O:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:4]2[C:5]3[S:9][CH:8]=[CH:7][C:6]=3[O:2][N:3]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 140972423-Thieno[2,3-d]isoxazol-3-yl-phenolHCID 21983578(2-Bromo-ethyl)-(3-fluorobenzyl)-amine

Product 1

HCID 9907296(3-Fluoro-benzyl)-[2-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-ethyl]-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add dichloromethane to 3-thieno[2,3-d]isoxazol-3-yl-phenol (10 g, 0.046 mol) or the appropriately protected 3-thieno[2,3-d]isoxazol-3-yl-phenol as is known in the art, and stir with sodium hydroxide (1M; 28 mL) to form the sodium salt. Combine the sodium salt from 3-thieno[2,3-d]isoxazol-3-yl-phenol, (2-bromo-ethyl)-(3-fluorobenzyl)-amine (37.5 g, 0.161 mol) in toluene (100 mL) and heat (reflux) for 24 hours. Allow to cool, filter the reaction mixture and evaporate off the solvent to give the final, desired compound. Compound may be purified by distillation under reduced pressure.

Workup

  1. temperatureheat
  2. temperature(reflux) for 24 hours
  3. temperatureAllow to cool
  4. filtrationfilter the reaction mixture
  5. customevaporate off the solvent

Sources & evidence

ORD record
ord-39687a43224143b2a901aec5623ec2e7
Source dataset
uspto-grants-2006_08
Patent number
US07091199B1

Linked notes

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