Potassium Iodide → 2-(Ethylamino)-4,5-dimethylthiophene-3-carbonitrile

HRID 2076972Notes

Reaction equation

HRID 2076972 reaction equation
[CH2:1]([NH:8][C:9]1[S:10][C:11]([CH3:17])=[C:12]([CH3:16])[C:13]=1[C:14]#[N:15])[C:2]1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C(I)C>C(#N)C.C(OCC)(=O)C>[CH2:1]([NH:8][C:9]1[S:10][C:11]([CH3:17])=[C:12]([CH3:16])[C:13]=1[C:14]#[N:15])[CH3:2]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 3194512-(Benzylamino)-4,5-dimethylthiophene-3-carbonitrile

Product 1

HCID 574569162-(Ethylamino)-4,5-dimethylthiophene-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(benzylamino)-4,5-dimethylthiophene-3-carbonitrile (302 mg, 2.0 mmol), potassium carbonate (276 mg, 2.0 mmol), and a catalytic amount of potassium iodide in acetonitrile (1 mL) in a 20 mL microwave vial was added ethyl iodide (310 mg, 2.0 mmol). The reaction vial was placed in a microwave reactor for 15 minutes at 165° C. The reaction mixture was dissolved in ethyl acetate and washed with water and brine. The ethyl acetate portion was dried over sodium sulfate and solvent was evaporated under reduced pressure, and the product was purified by prep HPLC using acetonitrile/water as solvent. MS 181 (MH+).

Workup

  1. customThe reaction
  2. washwashed with water and brine
  3. dry with materialThe ethyl acetate portion was dried over sodium sulfate and solvent
  4. customwas evaporated under reduced pressure
  5. customthe product was purified by prep HPLC

Sources & evidence

ORD record
ord-0d70503bfb4c4173a1694950269a474d
Source dataset
uspto-grants-2011_04
Patent number
US07928111B2

Reaction notes

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