Ethanolamine → 2-[2-(Hydroxyethylamino)-5-thiadiazolyl]-1-methyl-5-nitroimidazole

HRID 462223

Reaction equation

HRID 462223 reaction equation
Cl[N:2]1[NH:6][CH:5]=[C:4]([C:7]2[N:8]([CH3:15])[C:9]([N+:12]([O-:14])=[O:13])=[CH:10][N:11]=2)[S:3]1.[CH2:16]([CH2:18][NH2:19])[OH:17]>O1CCOCC1>[OH:17][CH2:16][CH2:18][NH:19][N:2]1[NH:6][CH:5]=[C:4]([C:7]2[N:8]([CH3:15])[C:9]([N+:12]([O-:14])=[O:13])=[CH:10][N:11]=2)[S:3]1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 213908012-(2-Chloro-5-thiadiazolyl)-1-methyl-5-nitroimidazole

Product 1

HCID 213908472-[2-(Hydroxyethylamino)-5-thiadiazolyl]-1-methyl-5-nitroimidazole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture consisting of 4.9 gm., 0.02 mole, of 2-(2-chloro- 5-thiadiazoly)-1-methyl-5-nitroimidazole, 3.0 gm., 0.05 mole, of ethanolamine, and 50 ml. of p-dioxane is stirred at room temperature for twenty-four hours. The precipitate is collected, washed with aqueous sodium bicarbonate solution, dried and recrystallized from methanol to give the pure compound melting at 208°-209° C. Working up the mother liquors gives additional material, the total yield being 3.4 gm.

Workup

  1. customThe precipitate is collected
  2. washwashed with aqueous sodium bicarbonate solution
  3. customdried
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-94c382ef593f420b8f9d79b441cf0819
Source dataset
uspto-grants-1977_12
Patent number
US04065567

Linked notes

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