Potassium Carbonate → HCID 15728438, compound

HRID 1164714Notes

Reaction equation

HRID 1164714 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([N:12]2[C:16](=[O:17])[NH:15][C:14]([CH3:18])=[N:13]2)=[C:4]([F:19])[CH:3]=1.Br[CH2:21][CH2:22][CH2:23][F:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([N:12]2[C:16](=[O:17])[N:15]([CH2:21][CH2:22][CH2:23][F:24])[C:14]([CH3:18])=[N:13]2)=[C:4]([F:19])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67699Propane, 1-bromo-3-fluoro-HCID 136058520HCID 136058520, compound

Product 1

HCID 15728438HCID 15728438, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1.8 g (0.006 mole) of 1-[4-chloro-2-fluoro-5-(1-methylethoxy)phenyl]-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one, 1.8 g (0.013 mole) of 1-bromo-3-fluoropropane and 0.30 g (0.010 mole) of potassium carbonate in dimethylformamide was heated at 55°-65° C. for 16 hours. The reaction mixture was cooled to ambient temperature and poured into ice-water. The mixture was extracted with diethyl ether and the extract dried with magnesium sulfate. The extract was filtered and the filtrate concentrated under reduced pressure to a residual oil. The oil was subjected to column chromatography on silica gel using 9:1 methylene chloride:heptane as eluant. The appropriate fractions were combined and concentrated under reduced pressure to give 1.0 g of 1-[4-chloro-2-fluoro-5-(1-methylethoxy)phenyl]-4-(3-fluoropropyl)-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one as an oil.

Workup

  1. extractionThe mixture was extracted with diethyl ether
  2. dry with materialthe extract dried with magnesium sulfate
  3. filtrationThe extract was filtered
  4. concentrationthe filtrate concentrated under reduced pressure to a residual oil
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fff589474c0148a39821e2091cff4b52
Source dataset
uspto-grants-1990_03
Patent number
US04906284

Reaction notes

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