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

HRID 1730184

Reaction equation

HRID 1730184 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-thiadiazolyl)-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-8205c95380b8479a80f8528f3fc5165b
Source dataset
uspto-grants-1976_11
Patent number
US03991200

Linked notes

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