2-Amino-4-(1,1-dimethylethyl)-3-thiophenecarbonitrile → HCID 13770589, compound

HRID 236226Notes

Reaction equation

HRID 236226 reaction equation
[NH2:1][C:2]1[S: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:20])[C:15](Cl)=[O:16]>C1C=CC=CC=1>[Cl:20][CH2:19][CH2:18][CH:14]([CH3:13])[C:15]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]=1[C:7]#[N:8])=[O:16]

Participants

4

Reactant 2

HCID 5968662-Amino-4-(1,1-dimethylethyl)-3-thiophenecarbonitrileHCID 137705824-Chloro-2-methylbutanoyl chloride

Product 1

HCID 13770589HCID 13770589, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4.0 g of 2-amino-3-cyano-4-(1,1-dimethylethyl)thiophene and 4.0 g of 2-methyl-4-chlorobutyryl chloride dissolved with 100 ml benzene was refluxed for about 72 hours. The solvent was evaporated under reduced pressure and the residue was chromatographed while eluting with a 90/10 mixture of Skellysolve B/ethyl acetate. Fractions containing the major component were combined and the solvent was evaporated therefrom to afford 3.75 g of 4-chloro-N-[3-cyano-4-(1,1-dimethylethyl)-2-thienyl]-2-methylbutanamide. mp=115°-116° C. Yield 57%.

Workup

  1. temperaturewas refluxed for about 72 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was chromatographed
  4. washwhile eluting with a 90/10 mixture of Skellysolve B/ethyl acetate
  5. additionFractions containing the major component
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0c923ef2530f484bb4fe3910b74e78dd
Source dataset
uspto-grants-1987_02
Patent number
US04643758

Reaction notes

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