Chloroacetone → HCID 178489885, compound

HRID 746087Notes

Reaction equation

HRID 746087 reaction equation
Cl[CH2:2][C:3](=O)[CH3:4].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([NH2:17])=[NH:16])=[CH:10][CH:9]=1>C(Cl)(Cl)Cl>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][C:15]2[NH:17][CH:2]=[C:3]([CH3:4])[N:16]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 3762749HCID 3762749, compound

Product 1

HCID 178489885HCID 178489885, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of chloroacetone (5.27 g, 0.057 m) in CHCl3 (90 mL) was added to a stirred suspension of 4-methoxyphenylacetamidine (28.0 g, 0.17 m) in CHCl3 (470 mL) over 1 hour. The mixture was heated at reflux for 75 minutes and then stirred at ambient temperature for 43 hours. The mixture was filtered and the filtrate was concentrated under reduced pressure. The oily residue was chromatographed on alumina and eluted with CHCl3 to yield 8.14 g (71%) of I; m.p. 108°-109° C. (CHCl3 -C6H14).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 75 minutes
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe oily residue was chromatographed on alumina
  6. washeluted with CHCl3
  7. customto yield 8.14 g (71%) of I

Sources & evidence

ORD record
ord-69e5400e7abf44d18ed34069552c12fb
Source dataset
uspto-grants-1986_07
Patent number
US04602093

Reaction notes

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