Methanethiol → 2-(Methylthio)-4-(trifluoromethyl)benzonitrile

HRID 1634623Notes

Reaction equation

HRID 1634623 reaction equation
[CH3:1][SH:2].C(=O)([O-])[O-].[K+].[K+].[N+]([C:12]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15])([O-])=O>CC(C)=O>[CH3:1][S:2][C:12]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 11430Potassium CarbonateHCID 699022-Nitro-4-(trifluoromethyl)benzonitrile

Product 1

HCID 111068072-(Methylthio)-4-(trifluoromethyl)benzonitrileYield 88.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
20 °C

Procedure

Methanethiol (278 g, 5.78M) was added during 20 minutes to a stirred mixture of acetone (5 litres) and potassium carbonate (593 g, 4.29M) at −15° C. A solution of 2-nitro-4-trifluoromethylbenzonitrile (618 g, 2.86M) in acetone (500 ml) was added during 10 minutes. The mixture was allowed to warm to 20° C. with stirring for 23 hours and then heated at 55° C. for 2 hours to remove most of the methanethiol and then flushed with nitrogen for 4 hours. The mixture was poured onto ice/water, the solid filtered off, washed and dried to give 2-methylthio-4-trifluoromethylbenzonitrile (550 g). The yield of product was 89%.

Workup

  1. temperatureheated at 55° C. for 2 hours
  2. customto remove most of the methanethiol
  3. customflushed with nitrogen for 4 hours
  4. additionThe mixture was poured onto ice/water
  5. filtrationthe solid filtered off
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-95db8e0351254296a923f2902d456f55
Source dataset
uspto-grants-2003_01
Patent number
US06506926B1

Reaction notes

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