Thionyl Chloride → HCID 22349860, compound

HRID 896217Notes

Reaction equation

HRID 896217 reaction equation
[C:1]([C:5]1[N:10]=[C:9](O)[CH:8]=[C:7]([CH:12]([F:14])[F:13])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:17])=O.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([C:5]1[N:10]=[C:9]([Cl:17])[CH:8]=[C:7]([CH:12]([F:14])[F:13])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 178441870HCID 178441870, compound

Product 1

HCID 22349860HCID 22349860, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.8 g of 2-tert-butyl-4-hydroxy-6-difluoromethyl-pyrimidine (13.9 mmol) and 3 ml of thionylchloride were stirred 14 h at room temperature and an additional 3 h at 76° C. 20 ml of dichloromethane were added with cooling, followed by addition of 15 ml of a saturated aqueous solution of sodium bicarbonate. The organic layer was separated, dried over magnesium sulfate and the solvent was evaporated to yield the crude title compound which was purified by column chromatography on silica gel (dichloromethane/hexane 1:1) to yield 0.8 g of product.

Workup

  1. temperaturewith cooling
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated
  5. customto yield the crude title compound which
  6. customwas purified by column chromatography on silica gel (dichloromethane/hexane 1:1)

Sources & evidence

ORD record
ord-01d7a881801c46818be5878901fd579e
Source dataset
uspto-grants-2005_07
Patent number
US06919342B2

Reaction notes

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