Dimethylformamide → N,N-dimethyl-N-{2-[(4-nitrophenyl)thio]ethyl}amine

HRID 2236688Notes

Reaction equation

HRID 2236688 reaction equation
Cl.CN([CH:5]([SH:7])C)C.C(=O)([O-])[O-].[K+].[K+].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.[CH3:24][N:25]([CH3:28])[CH:26]=O>O>[CH3:24][N:25]([CH3:28])[CH2:26][CH2:5][S:7][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 22036395N,N-dimethylaminoethanethiol hydrochloride

Product 1

HCID 21204381N,N-dimethyl-N-{2-[(4-nitrophenyl)thio]ethyl}amineYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of N,N-dimethylaminoethanethiol hydrochloride (2.9 g, 14 mmol) in N,N-dimethylformamide (DMF) (70 mL) is added potassium carbonate (19 g, 140 mmol), followed by 4-fluoronitrobenzene (1.5 mL, 14 mmol). After stirring overnight at room temperature, the reaction mixture is diluted with water and extracted 3× with ethyl acetate. The combined extracts were washed five times with water and with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude oil is purified by flash chromatography (Isco 40 g Redi-Sep column, MeOH/CHCl3) to give N,N-dimethyl-N-{2-[(4-nitrophenyl)thio]ethyl}amine (2.3 g, 72%) as a golden oil.

Workup

  1. extractionextracted 3× with ethyl acetate
  2. washThe combined extracts were washed five times with water
  3. dry with materialwith saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude oil is purified by flash chromatography (Isco 40 g Redi-Sep column, MeOH/CHCl3)

Sources & evidence

ORD record
ord-ddda25bdc3124b2ba48f4f0b3b6cda05
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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