2-Aminothiophenol → HCID 19864589, compound

HRID 1200026Notes

Reaction equation

HRID 1200026 reaction equation
[Na].[C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[N:12])=[N:9][CH:10]=1)([OH:4])=[O:3].N[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[SH:20]>C(O)C>[S:20]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:12]=[C:11]1[C:8]1[CH:7]=[CH:6][C:5]([C:2]([OH:4])=[O:3])=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 27611086-Cyanopyridine-3-carboxylic acidHCID 5360545Sodium2×

Product 1

HCID 19864589HCID 19864589, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (7.7 mmol) is added to a flask containing 70 ml of ethanol. As soon as the sodium has dissolved, 7 mmol of 5-carboxy-2-cyanopyridine and 8.4 mmol of 2-amino-thiophenol are added and the solution is refluxed for 24 h. The solid formed is filtered off, redissolved in ethanol and water, the solution is made acidic (pH=3) with 2N HCl and evaporated. The residue is dissolved in 100 ml of hot ethyl acetate, the salts are filtered off and the filtrate on cooling gives crystals of the title compound, m.p. >300°.

Workup

  1. temperaturethe solution is refluxed for 24 h
  2. customThe solid formed
  3. filtrationis filtered off
  4. dissolutionredissolved in ethanol
  5. customevaporated
  6. dissolutionThe residue is dissolved in 100 ml of hot ethyl acetate
  7. filtrationthe salts are filtered off
  8. temperaturethe filtrate on cooling

Sources & evidence

ORD record
ord-72a6e9dff16640b282fffce2008197f9
Source dataset
uspto-grants-1990_02
Patent number
US04904675

Reaction notes

Loading…