Triphenylphosphine → HCID 117988838, compound

HRID 2201374Notes

Reaction equation

HRID 2201374 reaction equation
[CH2:1]([S:3][C:4]1[N:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]([NH:8][C:9]1[CH:14]=[C:13]([S:15][C:16]([F:19])([F:18])[F:17])[CH:12]=[CH:11][C:10]=1[OH:20])=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:20][C:10]3[CH:11]=[CH:12][C:13]([S:15][C:16]([F:19])([F:18])[F:17])=[CH:14][C:9]=3[N:8]=2)=[CH:21][CH:22]=[CH:23][N:24]=1)[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 22836032Bis(2-methoxyethyl) diazene-1,2-dicarboxylateHCID 117998109HCID 117998109, compound

Product 1

HCID 117988838HCID 117988838, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2.13 g of 2-ethylsulfanyl-N-[2-hydroxy-5-(trifluoromethylsulfanyl)phenyl]nicotinamide, 2.14 g of DMEAD, 2.24 g of triphenylphosphine and 20 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 1.52 g of 2-(2-ethylsulfanylpyridin-3-yl)-5-(trifluoromethylsulfanyl)benzoxazole (hereinafter, referred to as Compound of Present Invention 38).

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-a6f3dfe2c12d42cba3509bce5b7a493f
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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