Chlorodifluoromethane → HCID 15035227, compound

HRID 1656435Notes

Reaction equation

HRID 1656435 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl[CH:22]([F:24])[F:23]>[OH-].[Na+].O1CCOCC1.O>[F:23][CH:22]([F:24])[S:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 6372ChlorodifluoromethaneHCID 15035215HCID 15035215, compound

Product 1

HCID 15035227HCID 15035227, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

6-Mercapto-3-nitro-4-phenylquinoline (1.00 g) was dissolved in a mixture of 2N-sodium hydroxide (20 ml) and dioxane (20 ml), and into the solution was introduced chlorodifluoromethane gas for 2 hrs. at 75°-80° C. The reaction mixture was diluted with water and extracted with chloroform. The extract was washed with aqueous 2N-sodium hydroxide solution and water, dried over anhydrous magnesium sulfate, and distilled to remove the solvent. The residue was recrystallized from isopropyl ether to give 6-difluoromethylthio-3-nitro-4-phenylquinoline as yellow prisms. Yield 948 mg (80.5%). m.p. 101°-103° C.

Workup

  1. customat 75°-80° C
  2. extractionextracted with chloroform
  3. washThe extract was washed with aqueous 2N-sodium hydroxide solution and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-5f0c9974fd424ef7a79f5e611fc73226
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

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