Ethanol → HCID 178513359, compound

HRID 2197438Notes

Reaction equation

HRID 2197438 reaction equation
[O-]CC.[Na+].Cl.[NH2:6][OH:7].C(O)C.[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]#[N:17]>C1CCCCC1.CCCCC>[OH:7][NH:6][C:16]([C:12]1[S:11][CH:15]=[CH:14][CH:13]=1)=[NH:17]

Participants

6

Reactant 4

HCID 702EthanolHCID 660872-ThiophenecarbonitrileHCID 443297Hydroxyamine hydrochlorideHCID 2723922Sodium ethoxide

Product 1

HCID 178513359HCID 178513359, compound

Reagents, catalysts & solvents 1

HCID 21949758Cyclohexane pentaneSolvent

Procedure

A solution of sodium ethoxide (21% by weight in ethanol, 64.9 ml, 0.174 mol, 1.1 eq.), hydroxylamine hydrochloride (12.1 g, 0.174 mol, 1.1 eq.) and ethanol (100 ml) was refluxed for 30 minutes. Thiophene-2-carbonitrile (18.8 g; 0.172 mol; 1 eq.) was then added and the solution was refluxed continuously for 18 hours. The reaction was monitored by thin layer chromatography (TLC) (50/50 cyclohexane/pentane). The solution was evaporated under reduced pressure and the residue obtained triturated in water at pH 7. The aqueous phase, saturated beforehand with NaCl, was then extracted with ethyl ether (three times). The organic phases were combined, dried over MgSO4 and concentrated under reduced pressure to give a white powder.

Workup

  1. temperaturethe solution was refluxed continuously for 18 hours
  2. customThe solution was evaporated under reduced pressure
  3. customthe residue obtained
  4. customtriturated in water at pH 7
  5. extractionwas then extracted with ethyl ether (three times)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customto give a white powder

Sources & evidence

ORD record
ord-11c1277f76704e73836f23feea079440
Source dataset
uspto-grants-2012_12
Patent number
US08338599B2

Reaction notes

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