Sulfuric Acid → HCID 20026173, compound

HRID 1722915Notes

Reaction equation

HRID 1722915 reaction equation
S(=O)(=O)(O)[OH:2].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[C:14]1([C:17]#[N:18])[CH2:16][CH2:15]1>>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[C:14]1([C:17]([NH2:18])=[O:2])[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 20026183Cyclopropanecarbonitrile, 1-(2-chloro-6-fluorophenyl)-

Product 1

HCID 20026173HCID 20026173, compound

Procedure

A reaction vessel containing 25 ml of concentrated sulfuric acid was cooled in ice bath. Then, 1-(2-chloro-6-fluorophenyl)cyclopropane carbonitrile (8.9 g, 0.046 mole) was slowly added to the reaction vessel. The reaction mixture was allowed to 15 warm to room temperature and stirred for 21/2 days. The mixture was poured into 100 ml of ice water mixture and then extracted with methylene chloride. The organic layer was washed with water (2×100 ml), brine (100 ml) and dried over magnesium sulfate. The solvent was removed and the product was chromatographed over 120 g silica gel with a cyclohexane:ethyl acetate (70:30) eluent to give 7.6 g of product (M.P. 98°-102° C.). ##STR6## where Xn =2-bromo

Workup

  1. temperaturewas cooled in ice bath
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with water (2×100 ml), brine (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed
  6. customthe product was chromatographed over 120 g silica gel with a cyclohexane:ethyl acetate (70:30) eluent

Sources & evidence

ORD record
ord-70e56d3225f5491a97cb12285b1235dd
Source dataset
uspto-grants-1989_08
Patent number
US04859232

Reaction notes

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