3-Chloro-2-butanone → HCID 12959396, compound

HRID 647521Notes

Reaction equation

HRID 647521 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Br:9])[C:3]=1[N:10]=[C:11]1[NH:15][CH2:14][CH2:13][NH:12]1.Cl[CH:17]([CH3:21])[C:18](=O)[CH3:19]>COCCO>[Br:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([Br:1])[C:3]=1[N:10]1[C:11]2=[N:12][CH2:13][CH2:14][N:15]2[C:18]([CH3:19])=[C:17]1[CH3:21]

Participants

4

Reactant 2

HCID 200263-Chloro-2-butanoneHCID 178422465HCID 178422465, compound

Product 1

HCID 12959396HCID 12959396, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

5.0 gm (0.015 mol) of 2-(2,6-dibromo-4-methyl-phenylimino)-imidazolidine were refluxed for about 30 hours with 1.8 gm (110%) of 96% 3-chloro-2-butanone in 25 ml of glycol monomethyl ether. The reaction mixture was then evaporated to dryness in vacuo, and the oily residue was dissolved in 1 N hydrochloric acid. The hydrochloric acid solution was adjusted to a pH value of 7 with dilute NaOH and, starting from the pH value, was fractionally extracted with ether at increasing pH values (NaOH). The ether extracts which were uniform according to thin-layer chromatography were combined, dried over magnesium sulfate, and the ether was eliminated in vacuo. The residual oil crystallized out after a short time. Yield: 0.4 gm of the compound of the formula ##STR10## corresponding to 7% of theory. Melting point: 154°-156° C.

Workup

  1. customThe reaction mixture was then evaporated to dryness in vacuo
  2. dissolutionthe oily residue was dissolved in 1 N hydrochloric acid
  3. extractionwas fractionally extracted with ether
  4. temperatureat increasing pH values (NaOH)
  5. dry with materialdried over magnesium sulfate
  6. customThe residual oil crystallized out after a short time

Sources & evidence

ORD record
ord-615d07bd2042411facced2260445c803
Source dataset
uspto-grants-1983_10
Patent number
US04409235

Reaction notes

Loading…