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

HRID 735076Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[OH:17].Cl.Cl[CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24]>CN(C=O)C>[Cl:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[O:17][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

112 g (0.81 mol) of potassium carbonate are added to a solution of 35 g (0.202 mol) of 2-chloro-4-nitrophenol in 350 mL of DMF. Then the reaction mixture is combined with 35 g (0.203 mol) of (2-chloroethyl)diethylamine hydrochloride and stirred for 3 hours at 80° C. and 14 hours at ambient temperature. The reaction mixture is evaporated down and the residue is poured onto 1000 mL of water and this mixture is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate, the desiccant is filtered off and the filtrate is evaporated down. Yield: 49.6 g (90% of theory); C12H17ClN2O3 (M=272.73); calc.: molecular ion peak (M+H)+: 273; found: molecular ion peak (M+H)+: 273; Rf value: 0.36 (silica gel, dichloromethane/methanol (90:10)).

Workup

customThe reaction mixture is evaporated down
additionthe residue is poured onto 1000 mL of water
extractionthis mixture is extracted three times with ethyl acetate
dry with materialThe combined organic phases are dried over sodium sulfate
filtrationthe desiccant is filtered off
customthe filtrate is evaporated down

Sources & evidence

ORD record: ord-0fdbce9b99ff41849e1d3ec6614fb88c
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592373B2

Reaction notes

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