Water → N,N-diethyl-2-[(4-nitrophenyl)thio]ethanamine

HRID 1164953Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[K+].Cl.Cl[CH2:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19].O>CN(C)C=O>[CH2:16]([N:17]([CH2:20][CH3:21])[CH2:18][CH2:19][S:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:15]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 7.0 g (45 mmol) of 4-nitrothiophenol and 22.5 mL of 4N aqueous potassium hydroxide in 40 mL of dimethylformamide add a solution of 9.53 g (55 mmol) of 2-chloro-N,N-diethylethanamine hydrochloride in 40 mL of dimethylformamide. Heat the reaction mixture for about 3 h at 100° C. After this time, cool the mixture to room temperature and add 150 mL of water. Extract th aqueous mixture with 3×200 mL of methylene chloride. Combine the methylene chloride extracts and extract these with 200 mL of 1N aqueous hydrochloric acid. Make the acid extract basic with saturated aqueous sodium bicarbonate solution

Workup

temperatureAfter this time, cool the mixture to room temperature
extractionExtract th aqueous mixture with 3×200 mL of methylene chloride
extractionextract these with 200 mL of 1N aqueous hydrochloric acid
extractionextract basic with saturated aqueous sodium bicarbonate solution

Sources & evidence

ORD record: ord-35996cfa0cc04334839e1a618a31634f
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04906634

Reaction notes

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