Thiophenol → HCID 19426995, compound

HRID 260430Notes

Reaction equation

HRID 260430 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-087e4d73e6e5457ebc24291496950a70
Source dataset
uspto-grants-1996_06
Patent number
US05527827

Reaction notes

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