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

HRID 1634622Notes

Reaction equation

HRID 1634622 reaction equation
[CH3:1][S-:2].[Na+].[N+]([C:7]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:8]=1[C:9]#[N:10])([O-])=O>CC(C)=O>[CH3:1][S:2][C:7]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:8]=1[C:9]#[N:10]

Participants

4

Reactant 2

HCID 699022-Nitro-4-(trifluoromethyl)benzonitrileHCID 4378561Sodium methanethiolate

Product 1

HCID 111068072-(Methylthio)-4-(trifluoromethyl)benzonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

Sodium thiomethoxide (366 g of a 21% aqueous solution, 1.1M) was added during 3 hours to a solution of 2-nitro-4-trifluoromethylbenzonitrile (220.5 g, 1.0M) in acetone (340 g) with stirring at 20-30° C. Stirring was continued for a further 1 hour and the two liquid phases separated. The upper layer (a solution of the product in acetone) was kept at 20° C. when 2-methylthio-4-trifluoromethylbenzonitrile crystallised (213 g), m.p.82° C. The yield was 97%, with product purity >96%.

Workup

  1. stirringStirring
  2. customthe two liquid phases separated
  3. customwas kept at 20° C.
  4. customcrystallised (213 g), m.p.82° C

Sources & evidence

ORD record
ord-d9fc9688ce1d49d78608aed162499263
Source dataset
uspto-grants-2003_01
Patent number
US06506926B1

Reaction notes

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