Dimethylformamide → 1-[(Ethylsulfanyl)methyl]-2-nitrobenzene

HRID 561368Notes

Reaction equation

HRID 561368 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Br)([O-:3])=[O:2].CN(C=O)C.[CH2:17]([S-:19])[CH3:18].[Na+]>O>[CH2:17]([S:19][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[CH3:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 77569alpha-Bromo-2-nitrotolueneHCID 4459711Sodium ethanethiolate

Product 1

HCID 583923871-[(Ethylsulfanyl)methyl]-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.0 g (46.3 mmol) of 2-nitrobenzyl bromide were introduced into 100 ml of DMF at 0° C., 3.89 g (46.3 mmol) of sodium ethanethiolate were added in portions, and the mixture was stirred at RT for 4 h. It was diluted with water and extracted with ethyl acetate, and the organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 9/1) to result in 7.40 g (81% of theory) of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 9/1)

Sources & evidence

ORD record
ord-a2a59b2d0dd64073a9cfbfc157502687
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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