Tetrahydrofuran → HCID 23632080, compound

HRID 884832Notes

Reaction equation

HRID 884832 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH:10][C:11](=[O:18])[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.N(C(OCC)=O)=NC(OCC)=O>O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]2[O:18][C:11]([C:12]3[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=3)=[N:10][C:3]=2[CH:4]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66880059HCID 66880059, compound

Product 1

HCID 23632080HCID 23632080, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1.17 g of N-(2-hydroxy-5-methoxyphenyl)isonicotinamide, 1.26 g of triphenylphosphine and 25 ml of tetrahydrofuran, a mixture of 0.85 g diethyl azodicarboxylate and 5 ml of tetrahydrofuran was added dropwise. The mixture was warmed to room temperature and stirred for four hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The combined organic layers were washed with water and a saturated sodium chloride solution, and dried over magnesium sulfate. Activated carbon was added thereto, which was filtered through Celite™. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.11 g of 5-methoxy-2-(pyridin-4-yl)-benzoxazole (hereinafter, referred to as “active compound 11”).

Workup

  1. additionwas added dropwise
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materiala saturated sodium chloride solution, and dried over magnesium sulfate
  5. additionActivated carbon was added
  6. filtrationwhich was filtered through Celite™
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-848f2ea9381441ba80e22f36f5e31226
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

Loading…