Ammonium Acetate → 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole

HRID 1416008Notes

Reaction equation

HRID 1416008 reaction equation
C([O-])(=O)C.[NH4+:5].[CH2:6]([O:13][CH2:14][C:15]([N:17]([CH:19]([S:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=1)[C:20](=O)[CH:21]([CH3:23])[CH3:22])[CH3:18])=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)(=O)C>[CH2:6]([O:13][CH2:14][C:15]1[N:17]([CH3:18])[C:19]([S:25][C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=2)=[C:20]([CH:21]([CH3:23])[CH3:22])[N:5]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 221306862-benzyloxy-N-[1-(3,5-dichlorophenylthio)-3-methyl-2-oxobutyl]-N-methylacetamide

Product 1

HCID 221305032-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In acetic acid was dissolved 2-benzyloxy-N-[1-(3,5-dichlorophenylthio)-3-methyl-2-oxobutyl]-N-methylacetamide (20), followed by addition of ammonium acetate, and the mixture was refluxed under heating. After 1 hour, the reaction mixture was concentrated under reduced pressure, neutralized with sodium hydroxide, and then, extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated to give 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-methylimidazole (17a).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9cbc54a4154e40f3b5711277c790668d
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

Loading…