Water → HCID 12112398, compound

HRID 1792781Notes

Reaction equation

HRID 1792781 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH:15]([CH3:17])[CH3:16])=[C:11]([CH2:13]I)[N:12]=1.[C-:18]#[N:19].[Na+].O>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH:15]([CH3:17])[CH3:16])=[C:11]([CH2:13][C:18]#[N:19])[N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 12112397HCID 12112397, compound

Product 1

HCID 12112398HCID 12112398, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In acetone (2 mL) was dissolved 2-(2-chlorophenyl)-4-iodomethyl-5-isopropyloxazole (590 mg, 1.63 mmol). Sodium cyanide (88 mg, 1.63 mmol) was added, and the resulting mixture was heated under reflux for 22 hours. The reaction mixture was cooled to room temperature, poured into water, and extracted with ethyl acetate. The organic layer was washed successively with water and a saturated brine, dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate=5/1), to obtain the desired compound (37 mg, 82%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 22 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed successively with water
  5. dry with materiala saturated brine, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-3b2e1627169841bba8a95cfd46efda70
Source dataset
uspto-grants-2006_07
Patent number
US07078422B2

Reaction notes

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