Dimethylformamide → HCID 11345951, compound

HRID 1072475Notes

Reaction equation

HRID 1072475 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([Cl:13])[C:5]=1[CH:14]([CH3:17])[C:15]#[N:16].[CH3:18]N(C=O)C>>[Cl:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([Cl:13])[C:5]=1[C:14]([CH3:18])([CH3:17])[C:15]#[N:16]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 22386574(+/-)-2,6-Dichloro-alpha-methyl4-nitrobenzeneacetonitrile

Product 1

HCID 11345951HCID 11345951, compound

Conditions

Temperature
0 °C

Procedure

NaH 80% (0.0918 mole) was added portionwise at 0° C. under N2 flow to a solution of intermediate (1) (0.0612 mole) in DMF (100 ml). The mixture was stirred at 0° C. under N2 flow for 1 hour. CH3l (0.0918 mole) was added dropwise at 0° C. The mixture was stirred at 50° C. for 12 hours, then poured out on ice and extracted with EtOAc. The organic layer was separated, washed with H2O, dried, filtered and the solvent was evaporated, yielding 17.1 g of 2,6-dichloro-α,α-dimethyl-4-nitrobenzeneacetonitrile (intermediate 2).

Workup

  1. additionCH3l (0.0918 mole) was added dropwise at 0° C
  2. stirringThe mixture was stirred at 50° C. for 12 hours
  3. additionpoured out on ice
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed with H2O
  7. customdried
  8. filtrationfiltered
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-84153eb9a1914c419ee40cdf7fc2faa9
Source dataset
uspto-grants-2005_06
Patent number
US06911444B2

Reaction notes

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