HCID 13770581, compound → 4-tert-Butyl-2-(3-methyl-2-oxopyrrolidin-1-yl)furan-3-carbonitrile

HRID 236224Notes

Reaction equation

HRID 236224 reaction equation
[NH2:1][C:2]1[O:3][CH:4]=[C:5]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]=1[C:7]#[N:8].[CH3:13][CH:14]([CH2:18][CH2:19]Cl)[C:15](Cl)=[O:16]>C1(C)C=CC=CC=1>[C:7]([C:6]1[C:5]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:4][O:3][C:2]=1[N:1]1[CH2:19][CH2:18][CH:14]([CH3:13])[C:15]1=[O:16])#[N:8]

Participants

4

Reactant 2

HCID 13770581HCID 13770581, compoundHCID 137705824-Chloro-2-methylbutanoyl chloride

Product 1

HCID 1748554-tert-Butyl-2-(3-methyl-2-oxopyrrolidin-1-yl)furan-3-carbonitrileYield 21.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 4.0 g of 2-amino-3-cyano-4-(1,1-dimethylethyl)furan and 4.3 g of 2-methyl-4-chlorobutyryl chloride was added 150 ml of toluene. The reaction mixture was allowed to reflux for about 72 hours. The mixture was washed once with 1N hydrochloric acid, once with 2N sodium hydroxide and finally with water. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue was chromatographed over silica gel while eluting with an 80/20 mixture of Skellysolve B/ethyl acetate. Fractions containing the major component were combined and the solvent was evaporated therefrom to afford 1.3 g of N-[3-cyano-4-(1,1-dimethylethyl)-2-furyl]-3-methyl-2-pyrrolidinone. mp=88°-90° C. Yield 21%.

Workup

  1. temperatureto reflux for about 72 hours
  2. washThe mixture was washed once with 1N hydrochloric acid, once with 2N sodium hydroxide and finally with water
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was chromatographed over silica gel
  7. washwhile eluting with an 80/20 mixture of Skellysolve B/ethyl acetate
  8. additionFractions containing the major component
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ee6519c414f943b6973ab1c04f62407c
Source dataset
uspto-grants-1987_02
Patent number
US04643758

Reaction notes

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