1-Chloro-4-nitrobenzene → HCID 15739784, compound

HRID 1415349Notes

Reaction equation

HRID 1415349 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[K+].[C:13]1([CH2:19][CH2:20][SH:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[C:13]1([CH2:19][CH2:20][S:21][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 14797Potassium HydroxideHCID 781262-Phenylethanethiol

Product 1

HCID 15739784HCID 15739784, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

75 g of 4-chloronitrobenzene in 300 ml of ethanol is heated to 70°. At this temperature there is then added dropwise 27 g of anhydrous potassium hydroxide and 65.9 g of 2-phenylethyl mercaptan in 250 ml of ethanol; the reaction mixture is refluxed for one hour and is then poured, with stirring into 1.5 liters of ice-water. The precipitated oil is extracted with methylene chloride, and the methylene chloride phases are dried over sodium sulphate. After purification through silica gel with methylene chloride as the eluant, there is obtained 4-(2'-phenyl-ethylthio)-nitrobenzene having a melting point of 35° - 37°.

Workup

  1. temperaturethe reaction mixture is refluxed for one hour
  2. additionis then poured
  3. extractionThe precipitated oil is extracted with methylene chloride
  4. dry with materialthe methylene chloride phases are dried over sodium sulphate
  5. customAfter purification through silica gel with methylene chloride as the eluant

Sources & evidence

ORD record
ord-3248757e5b504af681a83050ef32eda9
Source dataset
uspto-grants-1977_01
Patent number
US04004907

Reaction notes

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