Hydrochloric Acid → 3-chloro-1-[2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propoxy]-3-methyl-2-nitrosobutane

HRID 975616Notes

Reaction equation

HRID 975616 reaction equation
[CH3:1][C:2]([CH3:18])=[CH:3][CH2:4][O:5][CH2:6][CH:7]([OH:17])[CH2:8][N:9]1[CH:13]=[CH:12][N:11]=[C:10]1[N+:14]([O-:16])=[O:15].[N:19]([O:21]CCC(C)C)=O.[ClH:27]>>[Cl:27][C:2]([CH3:18])([CH3:1])[CH:3]([N:19]=[O:21])[CH2:4][O:5][CH2:6][CH:7]([OH:17])[CH2:8][N:9]1[CH:13]=[CH:12][N:11]=[C:10]1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 867504512-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl dimethylallyl ether

Product 1

HCID 222877343-chloro-1-[2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propoxy]-3-methyl-2-nitrosobutane

Procedure

To a cooled (0°-5° C.) stirred slurry of 1-[2-hydroxy-3-(2 -nitro-1H-imidazol-1-yl)propyl dimethylallyl ether (7.0 g, 0.0275 mol) in isoamyl nitrite (43 g, 50 mL, 0.042 mol) was added concentrated hydrochloric acid (2.5 mL, 0.03 mol) with stirring. The reaction mixture was maintained below 5° C. during the addition and stirred at 5° C. for an additional 2 hrs. The solid formed was stirred with cold ether-ethanol (3:1, 150 mL), filtered, and dried under vacuum. Yield: 5.8 g (67%). mp: 116°-117° C. dec. 1H NMR (DMSO) δ1.55 and 1.62 (s, 6H, CH3), 3.35 (m, 4H, CH2OCH2CHOH), 3.82 (m, 1H, CHOH), 4.1-4.52 (m, 2H, CHOHCH2N<), 5.3 (m, 1H, CHOH), 6.0 (dd, 1H, CHNO), 7.15 and 7.42 (s, 2H, imi H).

Workup

  1. temperatureTo a cooled (0°-5° C.)
  2. temperatureThe reaction mixture was maintained below 5° C. during the addition
  3. stirringstirred at 5° C. for an additional 2 hrs
  4. customThe solid formed
  5. filtrationfiltered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-2667c2800f1241b2b7b29ed9fcc2f111
Source dataset
uspto-grants-1997_03
Patent number
US05608110

Reaction notes

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