Sodium hydride → HCID 67157858, compound

HRID 548585Notes

Reaction equation

HRID 548585 reaction equation
[Cl:1][C:2]1[C:10](F)=[C:9]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[H-].[Na+].[Na].[CH3:19][O:20][CH2:21][CH2:22][SH:23]>CN(C=O)C.O>[Cl:1][C:2]1[C:10]([S:23][CH2:22][CH2:21][O:20][CH3:19])=[C:9]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 24758Sodium hydride2×HCID 30146442-Methoxyethanethiol2×HCID 5360545SodiumHCID 15451759HCID 15451759, compound

Product 1

HCID 67157858HCID 67157858, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

5.0 g (19.8 mmol) of 2-chloro-3-fluoro-4-methylsulfonylbenzoic acid (synthesis described in WO 98/42648) were taken up in 40 ml of DMF. 871 mg (21.8 mmol, purity 60% by weight) of NaH were added. The mixture was stirred at RT for 30 minutes. A reaction mixture containing the sodium salt of 2-methoxyethanethiol (prepared from a solution of 2.19 g (23.7 mmol) of 2-methoxyethanethiol in 10 ml of DMF which had been added dropwise to a suspension of 950 mg (23.7 mmol, purity 60% by weight) of NaH in 30 ml of DMF, followed by stirring at RT for 30 minutes) was then added a little at a time. During the addition, the temperature was kept below 30° C. The reaction mixture was stirred at RT for 16 h, for work-up diluted with water and washed with diethyl ether. The aqueous phase was acidified with 1M HCl and extracted with tert-butyl methyl ether. The organic phase was dried and filtered. The aqueous phase was additionally extracted with EA, and the organic phase was also dried and filtered. The filtrates of the organic phases were combined and freed from the solvent. The residue was dried under reduced pressure and purified chromatographically. This gave 4.8 g of the pure product.

Workup

  1. stirringby stirring at RT for 30 minutes)
  2. additionwas then added a little at a time
  3. additionDuring the addition
  4. customwas kept below 30° C
  5. stirringThe reaction mixture was stirred at RT for 16 h, for work-up
  6. washwashed with diethyl ether
  7. extractionextracted with tert-butyl methyl ether
  8. customThe organic phase was dried
  9. filtrationfiltered
  10. extractionThe aqueous phase was additionally extracted with EA
  11. customthe organic phase was also dried
  12. filtrationfiltered
  13. customThe residue was dried under reduced pressure
  14. custompurified chromatographically

Sources & evidence

ORD record
ord-1ba80ed8c325443eb43b9108121c2a79
Source dataset
uspto-grants-2011_05
Patent number
US07943551B2

Reaction notes

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