Ethanolamine → 3-Bromo-5-(2'-hydroxyethyl)amino-1-methyl-4-nitropyrazole

HRID 1376879Notes

Reaction equation

HRID 1376879 reaction equation
[Br:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5](Br)[N:4]([CH3:11])[N:3]=1.[CH2:12]([CH2:14][NH2:15])[OH:13].O>C(O)C>[Br:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5]([NH:15][CH2:14][CH2:12][OH:13])[N:4]([CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 962WaterHCID 229186383,5-Dibromo-1-methyl-4-nitro-1H-pyrazole

Product 1

HCID 229186243-Bromo-5-(2'-hydroxyethyl)amino-1-methyl-4-nitropyrazoleYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

3 g (10.5 mmoles) of 3,5-dibromo-1-methyl-4-nitropyrazole are heated in a solution of 30 ml ethanolamine in 30 ml ethanol for 15 hours at boiling temperature. The reaction mixture is then poured on 200 ml water, the separated product is filtered, washed with water (20 ml) and vacuum dried. Additional product crystallizes from the filtrate when cooled (5° C.). 2.25 g (81 percent of theory) of 3-bromo-5-(2'-hydroxyethyl)amino-1-methyl-4-nitropyrazole are obtained in the form of yellow crystals with a melting point of 150° C.

Workup

  1. filtrationthe separated product is filtered
  2. washwashed with water (20 ml) and vacuum
  3. customdried
  4. customAdditional product crystallizes from the filtrate when

Sources & evidence

ORD record
ord-934f0c9189c9415c8e6bfb115232ee5b
Source dataset
uspto-grants-1997_09
Patent number
US05663366

Reaction notes

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