Hydrochloric Acid → 3-Chloro-3-methyl-2-nitroso-1-(4-methyl-2-nitro-1H-imidazol-1-yl)butane

HRID 2393792Notes

Reaction equation

HRID 2393792 reaction equation
[ClH:1].[CH3:2][C:3]1[N:4]=[C:5]([N+:13]([O-:15])=[O:14])[N:6]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH:7]=1.[N:16]([O:18]CCC(C)C)=O>>[Cl:1][C:10]([CH3:12])([CH3:11])[CH:9]([N:16]=[O:18])[CH2:8][N:6]1[CH:7]=[C:3]([CH3:2])[N:4]=[C:5]1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 151860141-(4-methyl-2-nitro-1H-imidazol-1-yl)-3-methyl-2-butene

Product 1

HCID 151859953-Chloro-3-methyl-2-nitroso-1-(4-methyl-2-nitro-1H-imidazol-1-yl)butane

Conditions

Temperature
0 °C

Procedure

Concentrated HCl (20 mL) was added from an addition flask to a mixture of 1-(4-methyl-2-nitro-1H-imidazol-1-yl)-3-methyl-2-butene (5.0 g, 25.64) and isoamyl nitrite (20 mL), keeping the temperature in the range of 0° C. to 5° C. After the addition the reaction mixture was stirred at ice-cold temperature for 30 minutes. The solid which formed was removed by filtration and washed with ice-cold ethanol. The solid was dispersed in acetonitrile, cooled to 0 ° C. and filtered to provide the title product as a light blue colored solid; yield: 4.97 g (62%); mp. 110°-1130 ° C. (decomp); 1H NMR (DMSO-d6) δ 1.81[s, 6H, C(CH3)2 ], 2.16(s, 3H, imi-CH3), 5.36(s, 2H, NCH2), 7.12(s, 1H, imi-CH) and 11.98(s, 1H, NOH). MS m/e 261 (M+H)+.

Workup

  1. customin the range of 0° C. to 5° C
  2. additionAfter the addition the reaction mixture
  3. customThe solid which formed
  4. customwas removed by filtration
  5. washwashed with ice-cold ethanol
  6. additionThe solid was dispersed in acetonitrile
  7. filtrationfiltered

Sources & evidence

ORD record
ord-86d72c531744431ab85440517175ae22
Source dataset
uspto-grants-1998_09
Patent number
US05808091

Reaction notes

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