Chloroacetone → HCID 67915271, compound

HRID 2372289Notes

Reaction equation

HRID 2372289 reaction equation
[ClH:1].[Cl-].[CH3:3][N+:4]1[CH:8]=[C:7]([NH:9][C:10](=[O:20])[C@H:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH2:12])[N:6]([CH3:21])[C:5]=1[S:22][CH2:23][C:24](=[O:26])[CH3:25].[Cl:27]CC(=O)C>CC(C)=O>[ClH:27].[Cl-:1].[CH3:3][NH+:4]1[CH:8]=[C:7]([NH:9][C:10](=[O:20])[C@H:11]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH2:12])[N:6]([CH3:21])[CH:5]1[S:22][CH2:23][C:24](=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 6571Chloroacetone2×HCID 86745564HCID 86745564, compound

Product 1

HCID 67915271HCID 67915271, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,3-Dimethyl-4-([(L)-phenylalanyl]amino)-2-[(2-oxopropyl)thio]imidazolium chloride hydrochloride was then prepared: To a solution of 0.050 g (0.00128 mol) of the thione above prepared in 12 mL of acetone was added 0.12 g (0.0013 mol) of chloroacetone, and the solution was stirred 3 days. Additional chloroacetone (0.5 mL) was added at this time and the solution was stirred and refluxed for 24 hours. The solution was concentrated under vacuum and the residue was stirred with 5 mL of ethanol saturated with HCl (gas) for 6 hours. The solution was concentrated under vacuum and the residue was crystallized from isopropyl alcohol ether to obtain the desired 1,3-dimethyl-4-([(L)-phenylalanyl]amino)-2-[(2-oxopropyl)thio]-1H-imidazolium chloride hydrochloride; m.p. indeterminate at 90°-100° C. (softens, then foams).

Workup

  1. stirringthe solution was stirred
  2. temperaturerefluxed for 24 hours
  3. concentrationThe solution was concentrated under vacuum
  4. stirringthe residue was stirred with 5 mL of ethanol saturated with HCl (gas) for 6 hours
  5. concentrationThe solution was concentrated under vacuum
  6. customthe residue was crystallized from isopropyl alcohol ether

Sources & evidence

ORD record
ord-4487e2b02bdd4009a239a7dec0793c20
Source dataset
uspto-grants-1992_03
Patent number
US05098707

Reaction notes

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