Hydrochloric Acid → 3-chloro-3-methyl-1-(2-nitro-1H-imidazol-1-yl acetamido)-2-butanone oxime

HRID 2256787Notes

Reaction equation

HRID 2256787 reaction equation
[CH3:1][C:2]([CH3:17])=[CH:3][CH2:4][NH:5][C:6](=[O:16])[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[N+:13]([O-:15])=[O:14].[ClH:18].[N:19]([O:21]CCC(C)C)=O>>[Cl:18][C:2]([CH3:17])([CH3:1])[C:3](=[N:19][OH:21])[CH2:4][NH:5][C:6](=[O:16])[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8053Isoamyl NitriteHCID 18929154N-(3-methyl-2-butenyl)-2-(2-nitro-1H-imidazol-1-yl)acetamide

Product 1

HCID 867504503-chloro-3-methyl-1-(2-nitro-1H-imidazol-1-yl acetamido)-2-butanone oxime

Procedure

N-(3-methyl-2-butenyl)-2-(2-nitro-1H-imidazol-1-yl)acetamide (3.4 g, 14.3 mmol) was dissolved in isoamyl nitrite (50 mL) at room temperature. The solution was cooled to 0°-5° C. in an ice-salt bath. Concentrated HCl (1.39 mL) was added dropwise. The reaction temperature was maintained between 0° to 5° C. during the addition of HCl. The reaction mixture was stirred in the ice-salt bath for 1 h, filtered, and washed with 1:2 ethanol-ether to give a white solid.

Workup

  1. temperatureThe solution was cooled to 0°-5° C. in an ice-salt bath
  2. filtrationfiltered
  3. washwashed with 1:2 ethanol-ether
  4. customto give a white solid

Sources & evidence

ORD record
ord-79f10f4a237e412782fbafac165c8a6e
Source dataset
uspto-grants-1997_08
Patent number
US05656254

Reaction notes

Loading…