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

HRID 1164953
Notes
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Reaction equation

HRID 1164953 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 14797Potassium HydroxideHCID 158094-Nitrobenzenethiol

Product 1

HCID 19863411N,N-diethyl-2-[(4-nitrophenyl)thio]ethanamine

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

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

  1. temperatureAfter this time, cool the mixture to room temperature
  2. extractionExtract th aqueous mixture with 3×200 mL of methylene chloride
  3. extractionextract these with 200 mL of 1N aqueous hydrochloric acid
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes