Ethyl Acetate → HCID 22229400, compound

HRID 1355594Notes

Reaction equation

HRID 1355594 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 24, 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) resulted 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-089d4a35f86c40538392a7a945c48b67
Source dataset
uspto-grants-2003_07
Patent number
US06586405B2

Reaction notes

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