2-Chloro-6-methylbenzonitrile → 2-Mercapto-6-methylbenzonitrile

HRID 502602Notes

Reaction equation

HRID 502602 reaction equation
Cl[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5].C[S-:12].[Na+]>CN1CCCC1=O>[SH:12][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 230532-Chloro-6-methylbenzonitrileHCID 4378561Sodium methanethiolate

Product 1

HCID 162214682-Mercapto-6-methylbenzonitrileYield 33.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-chloro-6-methylbenzonitrile (3.00 g, 19.80 mmol), and sodium thiomethoxide (2.91 g, 41.58 mmol) in 1-methyl-2-pyrrolidinone (25 mL) was heated at 140° C. overnight. The reaction mixture was cooled to 0° C. and quenched with 50% aqueous HCl. A light yellow precipitate formed and the reaction was cooled for 1 h while stirring. The yellow solid was collected by vacuum filtration, washed with ice-cold water and dried under reduced pressure overnight to provide 2-mercapto-6-methylbenzonitrile (1.0 g). The crude product was carried forward without further purification. MW=149 confirmed by LC-MS, tr=2.98 min (Method E) MH+=150.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched with 50% aqueous HCl
  3. customA light yellow precipitate formed
  4. temperaturethe reaction was cooled for 1 h
  5. filtrationThe yellow solid was collected by vacuum filtration
  6. washwashed with ice-cold water
  7. customdried under reduced pressure overnight

Sources & evidence

ORD record
ord-272d9cb3da2844f7a99424df3bb51e6b
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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