Triphenylphosphine → HCID 118128227, compound

HRID 2201373Notes

Reaction equation

HRID 2201373 reaction equation
[CH2:1]([S:3][C:4]1[N:26]=[CH:25][CH:24]=[CH:23][C:5]=1[C:6]([NH:8][C:9]1[CH:14]=[C:13]([C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])[CH:12]=[CH:11][C:10]=1[OH:22])=O)[CH3:2].COCCOC(/N=N/C(OCCOC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[NH4+]>C1COCC1>[CH2:1]([S:3][C:4]1[C:5]([C:6]2[O:22][C:10]3[CH:11]=[CH:12][C:13]([C:15]([F:21])([F:20])[C:16]([F:18])([F:19])[F:17])=[CH:14][C:9]=3[N:8]=2)=[CH:23][CH:24]=[CH:25][N:26]=1)[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 22836032Bis(2-methoxyethyl) diazene-1,2-dicarboxylateHCID 117989049HCID 117989049, compound

Product 1

HCID 118128227HCID 118128227, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 0.57 g of 2-ethylsulfanyl-N-[2-hydroxy-5-(pentafluoroethyl)phenyl]nicotinamide, 0.54 g of DMEAD, 0.57 g of triphenylphosphine and 6 ml of THF was stirred at 50° C. for 4 hours. A saturated aqueous ammonium chloride solution was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.35 g of 2-(2-ethylsulfanylpyridin-3-yl)-5-(pentafluoroethyl)benzoxazole (hereinafter, referred to as Compound of Present Invention 36).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fc203a8b5c9847a9a428782778c0b238
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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