Thionyl Chloride → HCID 23364532, compound

HRID 1081414Notes

Reaction equation

HRID 1081414 reaction equation
O[CH2:2][C:3]([NH:6][C:7](=[O:21])[C:8]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[C:10]([C:16]([F:19])([F:18])[F:17])[C:9]=1[F:20])([CH3:5])[CH3:4].S(Cl)(Cl)=O.[H-].[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[F:20][C:9]1[C:10]([C:16]([F:17])([F:18])[F:19])=[C:11]([F:15])[C:12]([F:14])=[CH:13][C:8]=1[C:7]1[O:21][CH2:5][C:3]([CH3:4])([CH3:2])[N:6]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 23364529HCID 23364529, compound

Product 1

HCID 23364532HCID 23364532, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5.81 g (18.4 mmol) of N-(2-hydroxy- 1,1-dimethylethyl)-2, 4,5-trifluoro-3-(trifluoromethyl)benzamide in 100 mL of chloroform at 0° C. was treated dropwise with 5 mL of thionyl chloride. The mixture was allowed to warm to room temperature overnight. The solution was concentrated to a yellow oil which was dissolved in 20 mL of DMF and treated with 0.8 g (21.6 mmol) of 60% sodium hydride. This reaction mixture was stirred at room temperature for 18 hours, then poured into 50 mL of dilute NaHCO3. The solution was extracted with ethyl acetate; the organic phase was washed with water and dried over magnesium sulfate. Concentration in vacuo gave an orange oil which was chromatographed on silica, eluting with 2% methanol in chloroform, to give 2.62 g of a yellow oil.

Workup

  1. concentrationThe solution was concentrated to a yellow oil which
  2. dissolutionwas dissolved in 20 mL of DMF
  3. extractionThe solution was extracted with ethyl acetate
  4. washthe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationConcentration in vacuo
  7. customgave an orange oil which
  8. customwas chromatographed on silica
  9. washeluting with 2% methanol in chloroform

Sources & evidence

ORD record
ord-e35e8f2f0db445678c6dc2dcda2760dd
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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