Triphenylphosphine → 4-{2-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-2-chloro-benzonitrile

HRID 2233573Notes

Reaction equation

HRID 2233573 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[S:8][C:9]=1[CH2:10][CH2:11][OH:12])[CH2:2][CH2:3][CH3:4].[Cl:23][C:24]1[CH:31]=[C:30](O)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>ClCCl>[CH2:1]([C:5]1[N:6]=[C:7]([C:13]2[CH:14]=[CH:15][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:17][CH:18]=2)[S:8][C:9]=1[CH2:10][CH2:11][O:12][C:30]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([Cl:23])[CH:31]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5927972-Chloro-4-hydroxybenzonitrileHCID 5462977Diethyl azodicarboxylateHCID 592961692-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethanol

Product 1

HCID 592961274-{2-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-2-chloro-benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an iced cooled solution of 1.1 g 2-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethanol dissolved in 50 ml dichloromethane were added 0.56 g commercially available 2-Chloro-4-hydroxybenzonitrile and 0.95 g triphenylphosphine. To this solution was added dropwise 0.57 ml Diethylazodicarboxylate. The cooling bath was removed and reaction mixture stirred at room temperature for six hours. The solvent was removed in vacuo and the residue purified by RP-HPLC to provide 400 mg 4-{2-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-2-chloro-benzonitrile as lyophilisate.

Workup

  1. customThe cooling bath was removed
  2. customreaction mixture
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by RP-HPLC

Sources & evidence

ORD record
ord-7716136ad17c4c23a8fd8f241f6a6837
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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