Phosphorus oxychloride → HCID 58431286, compound

HRID 1617396Notes

Reaction equation

HRID 1617396 reaction equation
[F:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[N+:9]([O-])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].P(Cl)(Cl)([Cl:18])=O.O.[OH-].[Li+]>O1CCCC1>[Cl:18][C:8]1[N:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[C:2]([F:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 168937Lithium hydroxide, monohydrateHCID 58431400HCID 58431400, compound

Product 1

HCID 58431286HCID 58431286, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-fluoro-2-(trifluoromethyl)isonicotinic acid 1-oxide (1.0 g, 4.4 mmol from Step A) in phosphoryl chloride (4 mL, 40 mmol) was heated to 110° C. for 2 hours, then was left to stir at ambient temperature overnight. The POCl3 was evaporated, the residue was treated with sodium bicarbonate solution, which was stirred for 1 hour. To this mixture was added tetrahydrofuran (20 mL) and lithium hydroxide monohydrate (0.24 g, 5.7 mmol). This was stirred for 3 hours. The pH of the mixture was then adjusted to the range of pH 4-5 by the addition of c.HCl. The product was extracted with three portions of ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated. Yield: 0.54 g (50%); LC-MS: 244.1/245.9 (M+H)+. 1H NMR (300 MHz, CDCl3): δ 8.07 (d, 1H).

Workup

  1. waitwas left
  2. customThe POCl3 was evaporated
  3. additionthe residue was treated with sodium bicarbonate solution, which
  4. stirringwas stirred for 1 hour
  5. stirringThis was stirred for 3 hours
  6. additionThe pH of the mixture was then adjusted to the range of pH 4-5 by the addition of c
  7. extractionThe product was extracted with three portions of ethyl acetate
  8. dry with materialThe combined extracts were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-bb90b35bd84f4b71867eecb286c12273
Source dataset
uspto-grants-2014_07
Patent number
US08765734B2

Reaction notes

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