Potassium Carbonate → [2-(2-Chloro-4-nitro-phenoxy)-ethyl]-diethyl-amine

HRID 1820857Notes

Reaction equation

HRID 1820857 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:19]([N:21]([CH2:25][CH3:26])[CH2:22][CH2:23]Cl)[CH3:20]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH2:20][CH2:19][N:21]([CH2:25][CH3:26])[CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12074NitrofunginHCID 133631-Chloro-2-(diethylamine)ethane hydrochloride

Product 1

HCID 68816504[2-(2-Chloro-4-nitro-phenoxy)-ethyl]-diethyl-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

52.0 g (0.30 mol) of 2-chloro-4-nitrophenol is dissolved in 500 mL of DMF and 165 g (1.20 mol) of potassium carbonate is added batchwise. The mixture is stirred for 30 minutes at ambient temperature. Then 51.6 g (0.30 mol) of 2-diethylaminoethylchloride hydrochloride is added and the mixture is stirred for 3 days at ambient temperature. After this time, the mixture is filtered off, the solvent is eliminated, the residue is taken up in ethyl acetate, and washed with water. The organic phase is filtered through aluminum oxide (activity 2-3) and concentrated by evaporation. Yield: 41.0 g (50% of theory); Rf value: 0.60 (silica gel, methylene chloride/methanol/ammonia=9:1:0.01); C12H17ClN2O3.

Workup

  1. stirringthe mixture is stirred for 3 days at ambient temperature
  2. filtrationAfter this time, the mixture is filtered off
  3. washwashed with water
  4. filtrationThe organic phase is filtered through aluminum oxide (activity 2-3)
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-23d35e926054425fa3e26e8c081fcd76
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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