Acetonitrile → HCID 21866489, compound

HRID 1582921Notes

Reaction equation

HRID 1582921 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>[C:7]([C:6]1[C:5]([CH3:9])=[C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:3][CH:2]=1)#[N:8]

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, during which process the temperature of the reaction mixture rose and gas was evolved vigorously. The mixture was stirred for seven hours at room temperature and concentrated on a rotary evaporator under a high vacuum, the residue was purified by column chromatography (eluant dichloromethane), and 9.1 g (48%) of the desired compound were obtained as yellow oil. 1H NMR (270 MHz, DMSO-d6): δ=1.3 (t, 3H), 2.55 (s, 3H), 4.3 (q, 2H), 8.8 (s, 1H).

Workup

  1. concentrationconcentrated on a rotary evaporator under a high vacuum
  2. customthe residue was purified by column chromatography (eluant dichloromethane)

Sources & evidence

ORD record
ord-8c6c920663434c479e37461591108648
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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