1,4-Dioxane → 2-[2-(2,2-Diethoxyethylamino)-5-thiadiazolyl]-1-methyl-5-nitroimidazole

HRID 1730192

Reaction equation

HRID 1730192 reaction equation
OCCN[N:5]1[NH:9][CH:8]=[C:7]([C:10]2[N:11]([CH3:18])[C:12]([N+:15]([O-:17])=[O:16])=[CH:13][N:14]=2)[S:6]1.[CH2:19]([O:21][CH:22]([O:25][CH2:26][CH3:27])[CH2:23][NH2:24])[CH3:20].O1CCOCC1>O>[CH2:19]([O:21][CH:22]([O:25][CH2:26][CH3:27])[CH2:23][NH:24][N:5]1[NH:9][CH:8]=[C:7]([C:10]2[N:11]([CH3:18])[C:12]([N+:15]([O-:17])=[O:16])=[CH:13][N:14]=2)[S:6]1)[CH3:20]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 695242,2-DiethoxyethylamineHCID 213908472-[2-(Hydroxyethylamino)-5-thiadiazolyl]-1-methyl-5-nitroimidazole

Product 1

HCID 213908052-[2-(2,2-Diethoxyethylamino)-5-thiadiazolyl]-1-methyl-5-nitroimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture composed of 9.8 g. of 2-(2-chloro-5-thiadiazole)-1-methyl-5-nitroimidazole, (Example 16), 11.0 g. of 2,2-diethoxyethylamine, and 250 ml. of dioxane is stirred and heated on the steam bath for 12 hours. It is then diluted with 500 ml. of cold water, cooled, and the precipitated yellow solid collected and dried. Recrystallization from 50% aqueous ethanol gives the pure compound melting at 154°-155° C.

Workup

  1. temperatureheated on the steam bath for 12 hours
  2. additionIt is then diluted with 500 ml
  3. customthe precipitated yellow solid collected
  4. customdried
  5. customRecrystallization from 50% aqueous ethanol

Sources & evidence

ORD record
ord-55998eae4d09467f9b4e4fd38f184870
Source dataset
uspto-grants-1976_11
Patent number
US03991200

Linked notes

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