Heptane → 4-(1,3-Oxazol-5-yl)benzonitrile

HRID 659738

Reaction equation

HRID 659738 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=[O:2].S([CH2:21][N+:22]#[C-:23])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].CCCCCCC>CO>[O:2]1[C:1]([C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=2)=[CH:23][N:22]=[CH:21]1

Participants

6

Reactant 4

HCID 8900HeptaneHCID 11430Potassium CarbonateHCID 660424-CyanobenzaldehydeHCID 161915Tosylmethyl isocyanide

Product 1

HCID 27772714-(1,3-Oxazol-5-yl)benzonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-Formyl-benzonitrile (5 g, 38.17 mmol) and tosylmethyl isocyanide (TosMIC) (from Aldrich, 8.33 g, 42 mmol) in MeOH (200 mL) was added K2CO3 (6.85 g, 49.62 mmol) and the mixture was stirred at reflux for 1 h. The solvent was then evaporated and saturated aqueous NaHCO3 was added. The resultant suspension was extracted with dichloromethane (3×100 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous MgSO4 and concentrated to leave a yellow solid. Trituration with heptane afforded a solid that was collected by filtration and dried under vacuum to give the title compound (6.3 g, 97%). m.p.=140° C.

Workup

  1. temperatureat reflux for 1 h
  2. customThe solvent was then evaporated
  3. additionsaturated aqueous NaHCO3 was added
  4. extractionThe resultant suspension was extracted with dichloromethane (3×100 mL)
  5. washThe combined organic layers were washed with brine (30 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated
  8. customto leave a yellow solid
  9. filtrationthat was collected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-ee884524aae24f788390cbf66120db83
Source dataset
uspto-grants-2011_12
Patent number
US08080669B2

Linked notes

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