Thionyl Chloride → HCID 17963974, compound

HRID 1375026Notes

Reaction equation

HRID 1375026 reaction equation
O[CH2:2][C:3]([NH:6][C:7](=[O:19])[C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([I:18])[CH:9]=1)([CH3:5])[CH3:4].S(Cl)(Cl)=O>>[I:18][C:10]1[CH:9]=[C:8]([C:7]2[O:19][CH2:2][C:3]([CH3:4])([CH3:5])[N:6]=2)[CH:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:11]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 17963842HCID 17963842, compound

Product 1

HCID 17963974HCID 17963974, compoundYield 82.5%

Procedure

To N-(2-hydroxy-1,1-dimethylethyl)-3-iodo-5-(trifluromethyl)benzamide (2.11 g) was added thionyl chloride (1.29 ml), and the mixture was stirred at room temperature for 4 hours. The mixture was concentrated under reduced pressure, quenched with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate (X2). The combined extracts were dried over magnesium sulfate, evaporated, and purified with column chromatography (silica gel, ethyl acetate:hexane=2.5:97.5) to give 2-[3-iodo-5-(trifluoromethyl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole (1.66 g) as a solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customquenched with saturated aqueous sodium hydrogen carbonate solution
  3. extractionextracted with ethyl acetate (X2)
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. customevaporated
  6. custompurified with column chromatography (silica gel, ethyl acetate:hexane=2.5:97.5)

Sources & evidence

ORD record
ord-0a4bff92fd3f436087e24fa6c778339a
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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