Carbon Tetrachloride → HCID 51030999, compound

HRID 1913603Notes

Reaction equation

HRID 1913603 reaction equation
[Cl:1][C:2]1[CH:21]=[N:20][CH:19]=[C:18]([Cl:22])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=1[OH:17])=O.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>[Cl:1][C:2]1[CH:21]=[N:20][CH:19]=[C:18]([Cl:22])[C:3]=1[C:4]1[O:17][C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]=2[N:6]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66879955HCID 66879955, compound

Product 1

HCID 51030999HCID 51030999, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.35 g of 3,5-dichloro-N-(2-hydroxy-5-trifluoromethylphenyl)isonicotinamide, 5 ml of carbon tetrachloride, 0.78 g of triphenylphosphine and 0.30 g of triethylamine was heated to reflux for three hours. The mixture was cooled to room temperature, and then water was added to 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 concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.18 g of 2-(3,5-dichloropyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 17”).

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-9e45a7cb2eb043fa9361d5ab9f1ba166
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

Loading…