Thiophenol → HCID 19426995, compound

HRID 741809Notes

Reaction equation

HRID 741809 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:10])[CH:5]=[C:6](F)[CH:7]=1.[C:16]1([SH:22])C=CC=CC=1.C[S-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH3:16][S:22][C:6]1[CH:5]=[C:4]([C:9]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:10])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 25517Ammonium ChlorideHCID 4378561Sodium methanethiolateHCID 19426944(3,5-Difluorophenyl)(thiazol-2-yl)methanone

Product 1

HCID 19426995HCID 19426995, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3,5-difluorophenyl)(thiazol-2-yl)methanone from Thiophenol 2, Step 2, (1.09 g, 4.84 mmol) in DMF (4.8 mL) was added sodium thiomethoxide (0.34 g, 4,84 mmol). The mixture was stirred for 4 h at r.t., then added to sat. aqueous NH4Cl (100 mL) and extracted with EtOAc. The combined organic layers were washed with brine and dried over anhydrous MgSO4. Evaporation of the solvent and chromatography using hexane:EtOAc (90:10) gave 0.80 g of the title product.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. customEvaporation of the solvent and chromatography

Sources & evidence

ORD record
ord-dff2d120cf6f4053bea63183b5d15f15
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

Loading…