Dimethylformamide → HCID 67099646, compound

HRID 1868891Notes

Reaction equation

HRID 1868891 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]#N)[CH:7]=[CH:8][C:9]=1[F:10].[CH3:14]I.C[N:17]([CH:19]=O)C>>[Cl:3][C:4]1[CH:5]=[C:6]([C:11]([CH3:12])([CH3:14])[C:19]#[N:17])[CH:7]=[CH:8][C:9]=1[F:10]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27737253-Chloro-4-fluorobenzyl cyanide

Product 1

HCID 67099646HCID 67099646, compound

Conditions

Temperature
0 °C

Procedure

NaH (60% dispersion in mineral oil, 13.3 g, 333 mmol) was suspended in DMF (151 mL, 151 mmol), cooled to 0° C., and then a solution of 3-chloro-4-fluorophenylacetonitrile (25.65 g, 151 mmol) and MeI (23.6 mL, 378 mmol) in DMF was added dropwise via addition funnel. The reaction mixture was slowly warmed to ambient temperature and stirred for 3 hours. The reaction mixture was quenched with water, diluted with 200 mL of diethyl ether, added to a separatory funnel, partitioned with water, washed with water (2×100 mL), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (21.01 g) as a colorless oil after flash chromatography.

Workup

  1. temperatureThe reaction mixture was slowly warmed to ambient temperature
  2. customThe reaction mixture was quenched with water
  3. additiondiluted with 200 mL of diethyl ether
  4. additionadded to a separatory funnel
  5. custompartitioned with water
  6. washwashed with water (2×100 mL)
  7. customseparated
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eb2f64dac90849f6821d2d9ce0d095b7
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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