Diethylethanolamine → Diethyl[2-(2-methyl-4-nitrophenoxy)ethyl]amine

HRID 735110Notes

Reaction equation

HRID 735110 reaction equation
[H-].[Na+].F[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[CH3:13].[CH2:14]([N:16]([CH2:20][CH3:21])[CH2:17][CH2:18][OH:19])[CH3:15]>CN(C=O)C>[CH2:14]([N:16]([CH2:20][CH3:21])[CH2:17][CH2:18][O:19][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[CH3:13])[CH3:15]

Participants

5

Reactant 3

HCID 7497DiethylethanolamineHCID 24758Sodium hydrideHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-

Product 1

HCID 68816853Diethyl[2-(2-methyl-4-nitrophenoxy)ethyl]amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

0.92 g (19.2 mmol) of sodium hydride (50% in oil) is added at 0° C. under an argon atmosphere to a solution of 2.70 g (17.4 mmol) of 2-fluoro-5-nitrotoluene and 2.54 mL (19.2 mmol) of 2-diethylaminoethanol in 50 mL of DMF and the mixture is stirred for 2 hours at 0° C. and for 1 hour at ambient temperature. The solvent is removed, the residue is taken up in ethyl acetate, and extracted with water. The organic phase is dried over sodium sulfate and evaporated down in vacuo. Then it is purified by silica gel column chromatography with dichloromethane/methanol (9:1) as eluant. Yield: 3.1 g (71% of theory); C13H20N2O3 (M=252.31); calc.: molecular ion peak (M+H)+: 253; found: molecular ion peak (M+H)+: 253; Rf value: 0.60 (silica gel, dichloromethane/methanol (9:1)).

Workup

  1. customThe solvent is removed
  2. extractionextracted with water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated down in vacuo
  5. customThen it is purified by silica gel column chromatography with dichloromethane/methanol (9:1) as eluant

Sources & evidence

ORD record
ord-ea1275a7368e401c95427612ac16f755
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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