Triphenylphosphine → HCID 66880041, compound

HRID 1913609Notes

Reaction equation

HRID 1913609 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13](=[O:21])[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH-].[Na+]>O.C1(C)C=CC=CC=1.O1CCCC1>[CH3:20][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:14]=1[C:13]1[O:21][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][C:3]=2[N:12]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66879593HCID 66879593, compound

Product 1

HCID 66880041HCID 66880041, compoundYield 81.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 0.38 g of N-[2-hydroxy-5-(trifluoromethyl)phenyl]-3-methylisonicotinamide, 5 ml of tetrahydrofuran and 0.42 g of triphenylphosphine, 0.69 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature and stirred while heating at 60° C. After three hours, 5 ml of 10% aqueous solution of sodium hydroxide was added and stirred while heating at 60° C. for two hours. The reaction mixture was cooled to room temperature, and then water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.29 g of 2-(3-methylpyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 23”).

Workup

  1. additionwas added dropwise at room temperature
  2. stirringstirred
  3. temperaturewhile heating at 60° C. for two hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. extractionfollowed by extraction with ethyl acetate twice
  6. washThe combined organic layers were washed with a saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b26e419c97a47b184b896db5163db08
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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