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

HRID 1628575Notes

Reaction equation

HRID 1628575 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-c0d028c8925f47b19c4329bcb3b5aa31
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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