Lawesson's reagent → HCID 86656483, compound

HRID 75763Notes

Reaction equation

HRID 75763 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:20]=[C:19]([C:21]([NH2:23])=O)[O:18][N:17]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>O1CCOCC1>[F:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:20]=[C:19]([C:21](=[S:35])[NH2:23])[O:18][N:17]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86656482HCID 86656482, compound

Product 1

HCID 86656483HCID 86656483, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-[4-(6-fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carboxylic acid amide (3.54 g; 10 mmol) in dioxane (25 ml), was added Lawesson's reagent (4.11 g; 10 mmol) and the resulting reaction mixture was refluxed for 45 min. The pH of the reaction mixture was adjusted to near neutral, the solvent was removed and the residue was diluted with water (20 ml) and extracted with EtOAc (3×30 ml). The EtOAc layer was washed with water (3×10 ml) followed by brine (10 ml), and dried over anhydrous Na2SO4. The solvent was removed, and the residue was triturated with dichloromethane, filtered and dried to afford 3.0 g (80%) of the title compound. Mass (ES−), 369 (M−1); IR (KBr): 3282 (br), 3142 (br), 1651, 1608, 1588, 1555, 1441 (br); 1H NMR (DMSO-d6) δ: 7.18 (m, 1H), 7.58 (s, 1H), 7.65 (m, 1H), 7.77 (m, 1H), 7.88-7.94 (br, 4H), 7.97, 10.33 (2×br, 2H), 10.79 (s, 1H).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 45 min
  3. customthe solvent was removed
  4. additionthe residue was diluted with water (20 ml)
  5. extractionextracted with EtOAc (3×30 ml)
  6. washThe EtOAc layer was washed with water (3×10 ml)
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe solvent was removed
  9. customthe residue was triturated with dichloromethane
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-ec8ca7d9b6ab40daa5f253ef724e6b68
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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