4-Chloro-3-nitrotoluene → HCID 58521833, compound

HRID 2390281Notes

Reaction equation

HRID 2390281 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C([O-])([O-])=O.[K+].[K+].[CH2:18]([SH:21])[CH2:19][CH3:20]>CN(C=O)C>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([S:21][CH2:18][CH2:19][CH3:20])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 69764-Chloro-3-nitrotolueneHCID 7848Propyl mercaptanHCID 11430Potassium Carbonate

Product 1

HCID 58521833HCID 58521833, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 4-chloro-3-nitro-toluene (25 g, 145 mmol) in anhydrous DMF (200 ml) was treated with K2CO3 (40.29 g, 291 mmol) and 1-propane thiol (12.2 g, 160 mmol). The reaction mixture was heated to 70° C. for 12 h. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, diluted water and extracted with ethyl acetate (200 ml). The organic layer was washed with brine, dried over sodium sulphate and evaporated under reduced pressure, to give a crude which was purified by column chromatography (silica) using petroleum ether/ethyl acetate as eluent to afford the title compound (28 g, 91%) as a pale yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure, diluted water
  3. extractionextracted with ethyl acetate (200 ml)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure
  7. customto give a crude which
  8. customwas purified by column chromatography (silica)

Sources & evidence

ORD record
ord-14862c24d73b443ca133d29ea743abb2
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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