Aminomalononitrile p-toluenesulphonate → HCID 178510567, compound

HRID 1184866Notes

Reaction equation

HRID 1184866 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=O)/[CH:7]=[N:8]/[OH:9].C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:22][CH:23]([C:26]#[N:27])[C:24]#[N:25]>CC(O)C>[NH2:27][C:26]1[C:23]([C:24]#[N:25])=[N:22][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:7][N+:8]=1[O-:9]

Participants

4

Reactant 2

HCID 563049Aminomalononitrile p-toluenesulphonateHCID 12383845HCID 12383845, compound

Product 1

HCID 178510567HCID 178510567, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of (E)-2-(furan-2-yl)-2-oxoacetaldehyde oxime 54 (2.52 g, 18.12 mmol) and aminomalononitrile p-toluenesulfonate (4.59 g, 18.12 mmol) in 2-Propanol (35 mL) was stirred at rt for 70 h. Cooled down with ice bad with stirring. The resulting precipitate was collected by filtration, washed with 2-propanol and dried to give 2-amino-3-cyano-5-(furan-2-yl)pyrazine 1-oxide 55 (3.37 g, 92%). NMR (400 MHz, DMSO-d6) 6.65 (m, 1H), 7.10 (m, 1H), 7.83 (m, 1H), 8.09 (br s, 2H), 8.87 (s, 1H).

Workup

  1. temperatureCooled down with ice bad
  2. stirringwith stirring
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with 2-propanol
  5. customdried

Sources & evidence

ORD record
ord-f7adbf081bb748829bc48d0e78c5cb63
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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