Reaction #4853

ord-e4c770bdf0d9415a9eb6b135abc8f215

Reaction equation

O=[N+]([O-])c1cc2c(c([N+](=O)[O-])c1)OCC2
2,3-dihydro-5,7-dinitrobenzofuran
NCCO
2-aminoethanol
→
O=[N+]([O-])c1cc(CCO)c(NCCO)c([N+](=O)[O-])c1
expected product
O=[N+]([O-])c1cc(CCO)c(NCCO)c([N+](=O)[O-])c1
2-[2-(β-hydroxyethyl)amino-3,5-dinitrophenyl]ethanol

Reactants

O=[N+]([O-])c1cc2c(c([N+](=O)[O-])c1)OCC2
2,3-dihydro-5,7-dinitrobenzofuran
NCCO
2-aminoethanol

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONAfter the addition
  2. 2
    Temperatureafter the mixture is cooled

Procedure

0.29 Mole (60.9 g) of 2,3-dihydro-5,7-dinitrobenzofuran is added in small portions at room temperature to 122 ml of 2-aminoethanol. After the addition is complete, the reaction medium is brought for 15 minutes to 95° C. 500 ml of water are added; after the mixture is cooled, the expected product is drained, and this, after being made into a paste in water and recrystallized from 75 ml of 96° strength ethanol, melts at 115° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04727192uspto-grants-1988_02