Dimethylformamide → 3,5-Dimethylbenzonitrile

HRID 1804689

Reaction equation

HRID 1804689 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([NH2:7])=O.S(Cl)(Cl)=O.CN(C=O)C.[OH-].[Na+]>C1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]#[N:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 3194853,5-Dimethylbenzamide

Product 1

HCID 897183,5-DimethylbenzonitrileYield 95.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3,5-dimethylbenzamide (50 g, 0.3356 M) was suspended in benzene (400 mL). Thionyl chloride (49 mL, 0.671 M) and DMF (2 mL) were added and the mixture was refluxed for 2 hr. After cooling to room temperature, the mixture was poured into a crushed ice. After 1 hr., the solution was neutralized by the addition of 6 N sodium hydroxide solution. The product was then extracted with ether, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a yellow solid. The crude product was then purified by silica gel column chromatography (eluent, EA:hexane (1:4)) to afford 42 g (95%) of 3,5-dimethylbenzonitrile as a yellow solid. m.p. 51-52° C. 1H NMR (300 MHz, CDCl3) δ 2.34 (6H, s), 7.21 (1H, s), 7.26 (2H, s).

Workup

  1. temperaturethe mixture was refluxed for 2 hr
  2. extractionThe product was then extracted with ether
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a yellow solid
  7. customThe crude product was then purified by silica gel column chromatography (eluent, EA:hexane (1:4))

Sources & evidence

ORD record
ord-8edf7a50d5f94c12bcac03548062326b
Source dataset
uspto-grants-2013_01
Patent number
US08354421B2

Linked notes

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