Benzoyl chloride → 2-CYANO-6-PHENYLPYRIDINE

HRID 418052Notes

Reaction equation

HRID 418052 reaction equation
C[Si]([C:5]#[N:6])(C)C.C(Cl)(=O)[C:8]1[CH:13]=[CH:12]C=[CH:10][CH:9]=1.[CH:16]([NH:19][CH:20]([CH3:22])[CH3:21])([CH3:18])C.[C:23]([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:22]1([C:20]2[N:19]=[C:16]([C:5]#[N:6])[CH:18]=[CH:23][CH:21]=2)[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 7912DiisopropylamineHCID 10340Sodium CarbonateHCID 82115Trimethylsilyl cyanide

Product 1

HCID 27631452-CYANO-6-PHENYLPYRIDINE

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trimethylsilylcyanide (8 ml) was added to a solution of intermediate 38.1 (8.16 g) in DCM (95 ml). A solution of benzoyl chloride (7 ml) in DCM (50 ml) was added dropwise to the previous mixture. The reaction was stirred for 24 h at RT. Diisopropylamine (10.2 ml) was added and the reaction was stirred for 3 h. A Na2CO3 solution was added to the reaction mixture. The layers were separated and the aq. phase was extracted with DCM. The org. phases were combined, dried over Na2SO4 and evaporated off. The compound was purified by CC (EA/Hept 1/3) to afford 8.13 g of the desired product.

Workup

  1. stirringthe reaction was stirred for 3 h
  2. customThe layers were separated
  3. extractionthe aq. phase was extracted with DCM
  4. dry with materialdried over Na2SO4
  5. customevaporated off
  6. customThe compound was purified by CC (EA/Hept 1/3)

Sources & evidence

ORD record
ord-fe4884ac3a52464eafe3e62afd81fa30
Source dataset
uspto-grants-2012_01
Patent number
US08093250B2

Reaction notes

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