Ethanolamine → 2-(2,6-Dinitroanilino)ethan-1-ol

HRID 1398933Notes

Reaction equation

HRID 1398933 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].Cl[C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16]>O1CCCC1.C(OCC)(=O)C>[N+:12]([C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:15]([O-:17])=[O:16])[C:6]=1[NH:4][CH2:3][CH2:1][OH:2])([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 700EthanolamineHCID 118141-Chloro-2,6-dinitrobenzene

Product 1

HCID 233620182-(2,6-Dinitroanilino)ethan-1-olYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethanol amine (5.96 mL, 49.4 mmol) and 2-chloro-1,3-dinitrobenzene (5.00 g, 24.7 mmol) in tetrahydrofuran (50 mL) was stirred at room temperature for 2 h. The reaction mixture was diluted with ethyl acetate, washed with aqueous sodium hydrogen carbonate and brine, dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound as a brown solid (5.54 g, 24.4 mmol, 99%).

Workup

  1. washwashed with aqueous sodium hydrogen carbonate and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6a96eefc4a34e18a49c788788be6f08
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

Loading…