Potassium Carbonate → 4-[[2-(Diethylamino)ethyl]thio]benzenamine

HRID 1164954Notes

Reaction equation

HRID 1164954 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[CH2:4][CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[CH3:2].O.O.[Sn](Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[CH2:16]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][S:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1)[CH3:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 61436Stannous chloride dihydrateHCID 19863411N,N-diethyl-2-[(4-nitrophenyl)thio]ethanamine

Product 1

HCID 198633934-[[2-(Diethylamino)ethyl]thio]benzenamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 7.4 g (29 mmol) of N,N-diethyl-2-[(4-nitrophenyl)thio]ethanamine in 150 mL of ethanol add 32.8 g (140 mmol) of tin(II) chloride dihydrate. Reflux the reaction mixture for about 5 h. After this time, cool the reaction mixture to room temperature and carefully add the mixture to a solution of 75 g (0.54 mol) of potassium carbonate in 500 mL of water. Extract the mixture with 3×500 mL of ethyl acetate. Combine the organic extracts and wash with 2×350 mL of saturated aqueous sodium chloride solution. Dry the organic extracts over anhydrous sodium sulfate. Remov the drying agent by filtration and evaporate the solvent in vacuo to obtain the title compound.

Workup

  1. temperatureReflux the reaction mixture for about 5 h
  2. extractionExtract the mixture with 3×500 mL of ethyl acetate
  3. washwash with 2×350 mL of saturated aqueous sodium chloride solution
  4. dry with materialDry the organic extracts over anhydrous sodium sulfate
  5. customRemov the drying agent
  6. filtrationby filtration
  7. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-dcd8c592af6e47fb9304c6928fae98a8
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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