Iodoethane → HCID 14698850, compound

HRID 1165381Notes

Reaction equation

HRID 1165381 reaction equation
Cl[CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([N:13]3[C:17](=[O:18])[N:16]([CH2:19][CH2:20][CH2:21][F:22])[N:15]=[N:14]3)=[C:8]([F:12])[CH:9]=2)[NH:4][C:3]1=[O:23].C(=O)([O-])[O-].[K+].[K+].I[CH2:31][CH3:32]>CN(C)C=O>[CH2:31]([N:4]1[C:5]2[C:10](=[CH:9][C:8]([F:12])=[C:7]([N:13]3[C:17](=[O:18])[N:16]([CH2:19][CH2:20][CH2:21][F:22])[N:15]=[N:14]3)[CH:6]=2)[CH:11]=[CH:2][C:3]1=[O:23])[CH3:32]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 14698849HCID 14698849, compound

Product 1

HCID 14698850HCID 14698850, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.8 g (0.0052 mole) of 1-(3-chloro-6-fluoro-3,4-dihydroquinolin-2(1H)-one-7-yl)-4-(3-fluoropropyl)-1,4-dihydro-5H-tetrazol-5-one and 1.1 g (0.0079 mole) of potassium carbonate in 50 mL of dimethylformamide was stirred at room temperature for 30 minutes. To this solution was added 1.6 g (0.011 mole) of 2-iodoethane, and the reaction mixture was stirred at room temperature for one hour, then was heated at 40° C. for two days. The reaction mixture was heated at 70° C. for four hours, then was cooled and poured into icewater. This mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated under reduced pressure leaving a residue. This residue was purified by column chromatography on silica gel, eluting with ethyl acetate:n-hexane (75:25), to yield 0.77 g of 1[1 -ethyl-6-fluoroquinolin-2(1H)-one-7-yl]-4-(3-fluoropropyl)-1,4-dihydro-5H-tetrazol-5-one as an oil.

Workup

  1. temperaturewas heated at 40° C. for two days
  2. temperatureThe reaction mixture was heated at 70° C. for four hours
  3. temperaturewas cooled
  4. additionpoured into icewater
  5. extractionThis mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate was evaporated under reduced pressure
  9. customleaving a residue
  10. customThis residue was purified by column chromatography on silica gel
  11. washeluting with ethyl acetate:n-hexane (75:25)

Sources & evidence

ORD record
ord-d56e2444b45842fda9ea3f1e3f8a6997
Source dataset
uspto-grants-1990_03
Patent number
US04909829

Reaction notes

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