Water → HCID 56615066, compound

HRID 1256155Notes

Reaction equation

HRID 1256155 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1)(=O)=O.[CH3:17][S-:18].[Na+].O>CN(C=O)C>[CH3:17][S:18][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 219738843-Nitrophenethyl methanesulfonate

Product 1

HCID 56615066HCID 56615066, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-nitrophenethyl methanesulfonate (6 g, 24.5 m mol) in DMF (30 mL) was stirred at room temperature, then sodium methyl mercaptide (22 g, 20%) was added, followed by stirring at 70° C. overnight. Water was added to terminate the reaction. The aqueous layer was extracted with ethyl acetate 3 times. The combined organic phase was washed with brine, dried over sodium sulfate and concentrated to give methyl(3-nitrophenethyl)sulfane (4.4 g, yield 91%). 1H NMR: 400 MHz CDCl3 δ 8.09-8.07 (m, 2H), 7.53-7.56 (m, 1H), 7.49-7.45 (m, 1H), 3.03-2.99 (m, 2H), 2.81-2.78 (m, 2H), 2.16 (s, 3H).

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionThe aqueous layer was extracted with ethyl acetate 3 times
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-05e9fd1eeda54e07b02839ccb0a0c74c
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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