3-Carbamoyl-5-methylisoxazole → 5-Methylisoxazole-3-carbothioamide

HRID 1597447Notes

Reaction equation

HRID 1597447 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([NH2:9])=O)[CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:19])=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7](=[S:19])[NH2:9])[CH:3]=1

Participants

4

Reactant 2

HCID 769813-Carbamoyl-5-methylisoxazoleHCID 87949Lawesson's reagent

Product 1

HCID 27995305-Methylisoxazole-3-carbothioamideYield 103.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 525 mg (4.16 mmol) of 5-methylisoxazole-3-carboxamide and 1.85 g (4.58 mmol, 1.1 equiv) of Lawesson's reagent in 15 mL of dry toluene was heated to reflux for 5 h, during which time the reaction mixture became a clear yellow color. The reaction mixture was cooled to RT and the solvent was removed in vacuo. Purification of the material by silica gel flash column chromatography using a gradient of hexane/EtOAc 5/1 to hexane/EtOAc 1/1 as eluent followed by trituration with acetonitrile, filtration to remove the solid Lawesson's reagent byproducts and removal of solvent afforded 614 mg of the title compound as a yellow oil: 1H NMR (CDCl3, 300 MHz) δ 8.05 (s, br, 2H), 6.52 (s, 1H), 2.46 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 h, during which time the reaction mixture
  3. customthe solvent was removed in vacuo
  4. customPurification of the material by silica gel flash column chromatography
  5. filtrationfollowed by trituration with acetonitrile, filtration
  6. customto remove
  7. customthe solid Lawesson's reagent byproducts and removal of solvent

Sources & evidence

ORD record
ord-20857f6974b045459e7c3f289a5bb704
Source dataset
uspto-grants-2001_09
Patent number
US06294580B1

Reaction notes

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