Chloroacetone → HCID 58170471, compound

HRID 1619152Notes

Reaction equation

HRID 1619152 reaction equation
C(=O)([O-])O.[K+].[I:6][C:7]1[CH:8]=[C:9]([C:14](=[NH:16])[NH2:15])[CH:10]=[CH:11][C:12]=1[CH3:13].Cl[CH2:18][C:19](=O)[CH3:20]>O1CCCC1.O>[I:6][C:7]1[CH:8]=[C:9]([C:14]2[NH:15][C:19]([CH3:20])=[CH:18][N:16]=2)[CH:10]=[CH:11][C:12]=1[CH3:13]

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 516893Potassium BicarbonateHCID 53404021HCID 53404021, compound

Product 1

HCID 58170471HCID 58170471, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium hydrogen carbonate (0.204 g, 2.0 mmol) was added to a solution of 3-iodo-4-methylbenzenecarboximidamide (preparation 59a, 0.53 g, 0.54 mmol) in tetrahydrofuran (5 mL) and water (1 mL) and the mixture was heated to reflux. Then 1-chloropropan-2-one (0.16 mL, 2.1 mmol) in tetrahydrofuran (2.50 mL) was added dropwise over 20 min and the mixture was refluxed overnight. The mixture was evaporated and the residue purified by flash chromatography (2:1 hexanes/ethyl acetate) to give the title compound (0.13 g, 22%) as a white solid.

Workup

  1. temperaturethe mixture was heated to reflux
  2. temperaturethe mixture was refluxed overnight
  3. customThe mixture was evaporated
  4. customthe residue purified by flash chromatography (2:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-784c5adeab7d4c9bbe9f5b39ba72fefa
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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