Tetrahydrofuran → 2-(Pyridin-4-yl)-5-(trifluoromethylthio)benzoxazole

HRID 884888Notes

Reaction equation

HRID 884888 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[N:18]1[CH:17]=[CH:16][C:15]([C:14]2[O:21][C:2]3[CH:7]=[CH:6][C:5]([S:8][C:9]([F:10])([F:11])[F:12])=[CH:4][C:3]=3[N:13]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 66880242HCID 66880242, compound

Product 1

HCID 668807602-(Pyridin-4-yl)-5-(trifluoromethylthio)benzoxazoleYield 26.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a mixture of 0.69 g of N-[2-hydroxy-5-(trifluoromethylthio)phenyl]isonicotinamide, 9 ml of tetrahydrofuran, and 0.63 g of triphenylphosphine, 1.05 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature and stirred for three hours. To the mixture, 0.21 g of triphenylphosphine and 0.35 g of 40% toluene solution of diethyl azodicarboxylate were added. The reaction mixture was stirred for further two hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and the resultant crystals were washed with methanol to give 0.17 g of 2-(pyridin-4-yl)-5-(trifluoromethylthio)benzoxazole (hereinafter, referred to as “active compound 76”).

Workup

  1. additionwas added dropwise at room temperature
  2. stirringThe reaction mixture was stirred for further two hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washthe resultant crystals were washed with methanol

Sources & evidence

ORD record
ord-d341af3698434b06b802e57d1f16a879
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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