4-Methoxybenzenethiol → HCID 12043581, compound

HRID 2303472Notes

Reaction equation

HRID 2303472 reaction equation
[C:1]([C:3]1[O:4][C:5]2[CH:16]=[C:15]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:14]=[CH:13][C:6]=2[C:7]=1OS(C)(=O)=O)#[N:2].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([SH:29])=[CH:25][CH:24]=1.[H-].[Na+]>C1COCC1.CN(C=O)C>[CH3:20][S:17]([C:15]1[CH:14]=[CH:13][C:6]2[C:7]([S:29][C:26]3[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=3)=[C:3]([C:1]#[N:2])[O:4][C:5]=2[CH:16]=1)(=[O:18])=[O:19]

Participants

6

Reactant 3

HCID 127654-MethoxybenzenethiolHCID 24758Sodium hydrideHCID 86585614HCID 86585614, compound

Product 1

HCID 12043581HCID 12043581, compoundYield 38.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirring solution of 14 (0.25 g) and 4-methoxybenzenethiol (0.4 g) in THF (20 mL) and DMF (5 mL) was treated with NaH (0.080 g). After 3 h, the reaction was quenched by careful addition of H2O, then diluted with 1:1 EtOAc/hexanes. The organic layer was washed with saturated aqueous NaHCO3, washed with water, washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (silica gel, 20:80 to 33:67 EtOAc/hexanes) gave 0.11 g of 6-methanesulfonyl-3-(4-methoxyphenylsulfanyl)-benzofuran-2-carbonitrile 35 as a solid; (m+H)+ 360.

Workup

  1. customthe reaction was quenched by careful addition of H2O
  2. additiondiluted with 1:1 EtOAc/hexanes
  3. washThe organic layer was washed with saturated aqueous NaHCO3
  4. washwashed with water
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4015d596514b49e1a804c35642de0973
Source dataset
uspto-grants-2002_08
Patent number
US06433005B1

Reaction notes

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