Hydrochloric Acid → (+/-)-2,6-Dichloro-alpha-methyl4-nitrobenzeneacetonitrile

HRID 1072474Notes

Reaction equation

HRID 1072474 reaction equation
Cl[CH:2]([CH3:5])[C:3]#[N:4].[Cl:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]([Cl:16])[CH:8]=1.[OH-].[Na+].Cl>CS(C)=O>[Cl:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]([Cl:16])[C:8]=1[CH:2]([CH3:5])[C:3]#[N:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12064Benzene, 1,3-dichloro-5-nitro-HCID 14798Sodium HydroxideHCID 5192252-Chloropropionitrile

Product 1

HCID 22386574(+/-)-2,6-Dichloro-alpha-methyl4-nitrobenzeneacetonitrileYield 40%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of 2-chloropropionitrile (0.2 mole) and 1,3-dichloro-5-nitrobenzene (0.2 mole) in DMSO (50 ml) was added dropwise at RT to a solution of NaOH (1 mole) in DMSO (150 ml) while the temperature was kept below 30° C. The mixture was stirred at RT for 1 hour, then poured out on ice and acidified with HCl. The precipitate was filtered off, washed with H2O and taken up in CH2Cl2. The organic solution was washed with H2O, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/cyclohexane 70/30). The pure fractions were collected and the solvent was evaporated, yielding 19.5 g (40%) of (±)-2,6-dichloro-α-methyl-4-nitrobenzeneacetonitrile (intermediate 1).

Workup

  1. customwas kept below 30° C
  2. additionpoured out on ice
  3. filtrationThe precipitate was filtered off
  4. washwashed with H2O
  5. washThe organic solution was washed with H2O
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/cyclohexane 70/30)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4f8e6c2289f545edb85c13e757db7926
Source dataset
uspto-grants-2005_06
Patent number
US06911444B2

Reaction notes

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