Ethyl Acetate → HCID 22229400, compound

HRID 1355604Notes

Reaction equation

HRID 1355604 reaction equation
[C:1]([C:3]1[S:4][C:5]([CH2:8]Br)=[CH:6][CH:7]=1)#[N:2].[N-:10]=[N+:11]=[N-:12].[Na+].C(OCC)(=O)C>CN(C=O)C.CCCCCC>[C:1]([C:3]1[S:4][C:5]([CH2:8][N:10]=[N+:11]=[N-:12])=[CH:6][CH:7]=1)#[N:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 105600165-(Bromomethyl)thiophene-2-carbonitrile2×

Product 1

HCID 22229400HCID 22229400, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

A solution of 2-cyano-5-(bromomethyl)thiophene (compound 3-3, 3.5 g, 17.3 mmol) and sodium azide (Aldrich, 1.7 g, 26 mmol) in DMF (Aldrich, 60 ml) was stirred at ambient temperature for 10 hours. Flash column chromatography (20% ethyl acetate in hexane) gave the title compound (2.35 g, 83%). TLC: Rf 0.48 (20% of ethyl acetate in hexane); 1H NMR (CDCl3): δ 4.56 (s, 2H), 7.01 (d, 1H, J=3.7 Hz), 7.55 (d, 1H, J=3.7 Hz).

Sources & evidence

ORD record
ord-527db6b621f449b7a79d8b37da25af4c
Source dataset
uspto-grants-2003_07
Patent number
US06586405B2

Reaction notes

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