Acrylonitrile → HCID 73047396, compound

HRID 1867910Notes

Reaction equation

HRID 1867910 reaction equation
[N:1]([C:4]1[O:8][C:7]([CH:9]=O)=[CH:6][CH:5]=1)=[N+]=[N-].Cl.[NH2:12][NH:13][C:14]([NH2:16])=[O:15].C(#N)C=C>C(O)C.C(O)C.O>[NH:13]([N:12]=[CH:9][C:7](=[O:8])[CH:6]=[CH:5][C:4]#[N:1])[C:14]([NH2:16])=[O:15]

Participants

6

Reactant 3

HCID 7855AcrylonitrileHCID 11236Semicarbazide hydrochlorideHCID 125701505-Azidofuran-2-carbaldehyde

Product 1

HCID 73047396HCID 73047396, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 19096565Water ethanolSolvent

Procedure

A solution of 5-azido-2-furaldehyde (92 mg, 0.67 mmole) in 4 ml of ethanol was added dropwise to a solution of semicarbazide hydrochloride (75 mg, 0.67 mmole) in 10 ml of ethanol:water (5:1) mixture. The reaction mix was stirred at room temperature overnight and evaporated to dryness. The residue was dissolved in 1.2 ml of acetone and streaked on one preparative silica gel TLC plates (EM-5717-7), developed with ethyl acetate:petroleum ether (9:1). Two well-separated major bands (upper band with Rf of 0.56 and lower band with Rf of 0.20) were detected under UV lights and were separately stripped and eluted with excess of ethyl acetate. The ethyl acetate eluents were evaporated to give pale yellow residues (45 mg and 35 mg, respectively). On silica gel TLC, both residues showed identical pattern of two distinctly separated spots with Rf of 0.56 and 0.33 when the TLC was developed with ethyl acetate:petroleum ether (6:1). The TLC analysis suggested that both residues contained interconvertible cis and trans isomers and were, therefore, combined (total yield 0.48, 72%). 1H NMR analysis of 2 confirmed that it is a mixture of two isomers with the acrylonitrile moiety in cis (Z) and trans (E)-configurations (coupling constant J=11.6 and 16.5 Hz, respectively).

Workup

  1. additionThe reaction mix
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in 1.2 ml of acetone
  4. washeluted with excess of ethyl acetate
  5. customThe ethyl acetate eluents were evaporated
  6. customto give pale yellow residues (45 mg and 35 mg
  7. custom(total yield 0.48, 72%)

Sources & evidence

ORD record
ord-c09be16c280a440cb55eb572e87b0973
Source dataset
uspto-grants-2009_12
Patent number
US07632928B2

Reaction notes

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