Hydrogen Peroxide → HCID 59295509, compound

HRID 2233307Notes

Reaction equation

HRID 2233307 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:10]=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=2)[S:5][C:6]=1[CH2:7][OH:8].[Cl:19][C:20]1[CH:27]=[C:26](O)[CH:25]=[CH:24][C:21]=1[C:22]#[N:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.OO>O1CCCC1.C(OCC)C>[Cl:19][C:20]1[CH:27]=[C:26]([O:8][CH2:7][C:6]2[S:5][C:4]([C:9]3[CH:10]=[N:11][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:14]=3)=[N:3][C:2]=2[CH3:1])[CH:25]=[CH:24][C:21]=1[C:22]#[N:23]

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 11776TriphenylphosphineHCID 5927972-Chloro-4-hydroxybenzonitrileHCID 5462977Diethyl azodicarboxylateHCID 59295476HCID 59295476, compound

Product 1

HCID 59295509HCID 59295509, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice cooled solution of 2.76 g [4-Methyl-2-(6-trifluoromethyl-pyridin-3-yl)-thiazol-5-yl]-methanol, 2.06 g 2-chloro-4-hydroxybenzonitrile and 3.03 g triphenylphosphine in 30 ml tetrahydrofuran were added 1.74 ml diethylazodicarboxyate. The reaction mixture was stirred at room temperature overnight. 0.56 ml 30% H2O2 were added and the reaction mixture diluted by addition of 200 ml diethylether. The organic layer was washed with 50 ml 1N NaOH and 50 ml water, dried over MgSO4. The solvent was removed in vacuo. The resulting residue was purified by reversed phase HPLC to obtain 2.02 g 2-Chloro-4-[4-methyl-2-(6-trifluoromethyl-pyridin-3-yl)-thiazol-5-ylmethoxy]-benzonitrile as a lyophilisate.

Workup

  1. washThe organic layer was washed with 50 ml 1N NaOH and 50 ml water
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customThe resulting residue was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-90ddb031086d4ebe8be4d5fd6fc90e26
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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