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

HRID 1779743Notes

Reaction equation

HRID 1779743 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=C=O.[N:22]([O:24]CCC(C)C)=O>>[Cl:18][C:2]([CH3:17])([CH3:1])[C:3](=[N:22][OH:24])[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

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6347Isocyanic acidHCID 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. Yield: 3.7 g (85%). mp: 154°-160° C. (decomp.). 1H NMR (DMSO-d6) ε 1.74 and 1.88 [s, 6H, =C(CH3)2 ], 4.17 (q, 2H, HNCH2CH=), 5.08 (s, 2H, COCH2 -imidazolyl), 5.14 (t, 1H, CH2CH=), 7.18 and 7.63 (s, 2H, 2-nitroimidazolyl-H), 8.51 (t, 1H, HNCO), 11.60 (b, 1H, HON=C).

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-5b4906956c9241e9b5808da4c4ff7511
Source dataset
uspto-grants-1997_05
Patent number
US05627286

Reaction notes

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