Acetonitrile → HCID 21866489, compound

HRID 1840719Notes

Reaction equation

HRID 1840719 reaction equation
N[C:2]1[S:3][C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].C(#N)C.N(OC(C)(C)C)=O>CN(C)C=O>[CH2:13]([O:12][C:10]([C:4]1[S:3][CH:2]=[C:6]([C:7]#[N:8])[C:5]=1[CH3:9])=[O:11])[CH3:14]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 10906Tert-Butyl nitriteHCID 610877ethyl 5-amino-4-cyano-3-methylthiophene-2-carboxylate

Product 1

HCID 21866489HCID 21866489, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 20.5 g (97.5 mmol) of ethyl 2-amino-3-cyano-4-methylthiophene-5-carboxylate in 600 ml of a 1:1 mixture of acetonitrile and dimethylformamide was cooled to 5° C., and 15.7 g (146 mmol) of tert-butyl nitrite were added dropwise, the reaction mixture heating up and vigorous gas evolution beginning. Stirring was carried out for seven hours at room temperature, the mixture was evaporated down in a rotary evaporator and under greatly reduced pressure, the residue was purified by column chromatography (mobile phase: dichloromethane) and 9.1 g (48%) of the desired compound were obtained as a yellow oil.

Workup

  1. temperaturethe reaction mixture heating up
  2. customthe mixture was evaporated down in a rotary evaporator and under greatly reduced pressure
  3. customthe residue was purified by column chromatography (mobile phase: dichloromethane)

Sources & evidence

ORD record
ord-b6414f9b05ab4c2eaa517cf7b452bc4f
Source dataset
uspto-grants-2004_01
Patent number
US06683055B1

Reaction notes

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