2-Bromopropane → HCID 14441918, compound

HRID 654401Notes

Reaction equation

HRID 654401 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]=[C:10]2[N:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]3[CH:12]([CH3:19])[O:11]2)=[C:4]([F:20])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:28]([CH3:30])[CH3:29]>CC(C)=O>[Cl:1][C:2]1[C:7]([O:8][CH:28]([CH3:30])[CH3:29])=[CH:6][C:5]([N:9]=[C:10]2[N:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]3[CH:12]([CH3:19])[O:11]2)=[C:4]([F:20])[CH:3]=1

Participants

5

Reactant 3

HCID 63582-Bromopropane2×HCID 11430Potassium CarbonateHCID 14441919HCID 14441919, compound

Product 1

HCID 14441918HCID 14441918, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3.5 g 3-(4-Chloro-2-fluoro-5-hydroxyphenylimino)-1-methylhexahydro-3H-oxazolo[3,4-a]pyridine and 6.6 g potassium carbonate in 40 ml acetone was treated at room temperature with 3.1 g 2-bromopropane and heated under reflux for 6 hours. It was then treated again with 3.1 g 2-bromopropane and heated under reflux for 6 hours. After cooling the mixture was filtered, the filtrate concentrated and the residue purified by column chromatography (silica gel, eluent; hexane/ethyl acetate).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. temperatureheated
  4. temperatureunder reflux for 6 hours
  5. temperatureAfter cooling the mixture
  6. filtrationwas filtered
  7. concentrationthe filtrate concentrated
  8. customthe residue purified by column chromatography (silica gel, eluent; hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9f8c18440f1a48e8b3305ae64a605516
Source dataset
uspto-grants-1992_07
Patent number
US05131946

Reaction notes

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