2-Propanethiol → HCID 67934946, compound

HRID 2248608Notes

Reaction equation

HRID 2248608 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.P(Cl)(Cl)(Cl)=O.C(N(CC)CC)C.[CH:34]([SH:37])([CH3:36])[CH3:35]>C1C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([S:37][CH:34]([CH3:36])[CH3:35])=[N:8][N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 63642-PropanethiolHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 19994966HCID 19994966, compound

Product 1

HCID 67934946HCID 67934946, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.83 g (8.9 mmol) of 4-fluoro-N-(1H-1,2,4-triazol-1-yl)-benzamide and 1.05 g (8.9 mmol) of phosphorous pentachloride and 20 mL of phosphorous oxychloride is heated at reflux for 1 h. Solvent is stripped and the residue dissolved in 30 mL of benzene. Triethylamine (1.4 mL, 10 mmol) and 1.0 g (13 mmol) of isopropyl mercaptan is added and the solution is heated at reflux for 4 h. The solution is diluted with ethyl acetate and washed with water and brine. Drying (MgSO4) and removal of solvent gives product which is purified by chromatography on silica gel.

Workup

  1. temperatureat reflux for 1 h
  2. temperaturethe solution is heated
  3. temperatureat reflux for 4 h
  4. washwashed with water and brine
  5. customDrying
  6. custom(MgSO4) and removal of solvent
  7. customgives product which
  8. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-aebfef610fdb41a382a9e0681e117644
Source dataset
uspto-grants-1991_08
Patent number
US05041458

Reaction notes

Loading…