2-Butanone, 3-bromo- → HCID 59457487, compound

HRID 1710749Notes

Reaction equation

HRID 1710749 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][CH:7]=1.Br[CH:16]([CH3:20])[C:17](=O)[CH3:18]>C(#N)CC>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]2[O:11][C:16]([CH3:20])=[C:17]([CH3:18])[N:12]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 131422-Butanone, 3-bromo-HCID 144071764-(3-Chloropropoxy)benzamide

Product 1

HCID 59457487HCID 59457487, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Procedure

A suspension of 4-(3-chloropropoxy)benzamide ax54 (1.2 g, 5.62 mmol) and 3-bromobutan-2-one (1.02 g, 6.74 mmol) is heated in propionitrile (50 ml) at reflux for 10 days. The mixture is then concentrated and the resulting black mixture is filtered through a pad of silicagel, eluting first with dichloromethane (100 ml) and then with a 96:4 mixture of dichloromethane and dimethoxymethane to afford two fractions. The second fraction is concentrated, and the resulting yellow solid (0.67 g) is further purified by chromatography over silicagel (eluent: dichloromethane) to afford 330 mg of 2-[4-(3-chloropropoxy)phenyl]-4,5-dimethyl-oxazole i30 as a pale yellow solid.

Workup

  1. temperatureat reflux for 10 days
  2. concentrationThe mixture is then concentrated
  3. filtrationthe resulting black mixture is filtered through a pad of silicagel
  4. washeluting first with dichloromethane (100 ml)
  5. additionwith a 96:4 mixture of dichloromethane and dimethoxymethane
  6. customto afford two fractions
  7. concentrationThe second fraction is concentrated
  8. customthe resulting yellow solid (0.67 g) is further purified by chromatography over silicagel (eluent: dichloromethane)

Sources & evidence

ORD record
ord-c5b6c9c6ff964fc893be6bf2ab618058
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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