Carbon Tetrachloride → HCID 58088036, compound

HRID 2190706Notes

Reaction equation

HRID 2190706 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=O)[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:7]([OH:20])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]2[N:11]=[C:12]([C:13]3[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=3)[O:20][C:7]=2[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 58148107HCID 58148107, compound

Product 1

HCID 58088036HCID 58088036, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.22 g of N-(4-tert-butyl-2-hydroxyphenyl)isonicotinamide, 15 ml of carbon tetrachloride, 3.55 g of triphenylphosphine and 1.37 g of triethylamine was heated to reflux for three hours. The mixture was cooled to room temperature, and then water was poured into the mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.30 g of 6-tert-butyl-2-(pyridin-4-yl)-benzoxazole (hereinafter, referred to as “active compound 8”).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for three hours
  3. extractionfollowed by extraction with ethyl acetate twice
  4. washThe combined organic layers were washed with a saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c8f0fe851645482eb26da72d21954c37
Source dataset
uspto-grants-2012_12
Patent number
US08324387B2

Reaction notes

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