Water → 5-[(Hydroxyimino)methyl]-3-thiophenecarbonitrile

HRID 1582900Notes

Reaction equation

HRID 1582900 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=O)[S:6][CH:7]=1)#[N:2].C(=O)([O-])[O-].[Na+].[Na+].Cl.[NH2:17][OH:18].O>CO>[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[N:17][OH:18])[S:6][CH:7]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 122800095-formylthiophene-3-carbonitrile

Product 1

HCID 738516325-[(Hydroxyimino)methyl]-3-thiophenecarbonitrileYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

11.6 g (84.6 mmol) of 4-cyanothiophene-2-carbaldehyde were dissolved in 140 ml of methanol and 12.3 g (116.1 mmol) of sodium carbonate were added. 6.5 [lacuna] (93.5 mmol) of hydroxylamine hydrochloride were subsequently added at 15° C. with cooling, a little at a time, and the mixture was stirred for 2 hours at 10° C. After 80 ml of water had been added, the reaction mixture was extracted five times using in each case 50 ml of diethyl ether, the organic phase was dried over sodium sulfate and the solvent was removed in vacuo. 12.5 g of the required product resulted as a yellow crystal powder (96% of theory).

Workup

  1. temperaturewith cooling
  2. extractionthe reaction mixture was extracted five times
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-428f6cf68ce44ccd90b0424d6b713a43
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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