Ethyl Acetate → HCID 22229400, compound

HRID 1263423Notes

Reaction equation

HRID 1263423 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 23, 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); 1HNMR (CDCl3) δ4.56 (s, 2H), 7.01 (d, 1H, J=3.7 Hz), 7.55 (d, 1H, J=3.7 Hz).

Sources & evidence

ORD record
ord-5d913382155745feb3406c3f101d9623
Source dataset
uspto-grants-2003_04
Patent number
US06541467B1

Reaction notes

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