Sodium Carbonate → HCID 15166285, compound

HRID 357568Notes

Reaction equation

HRID 357568 reaction equation
[CH3:1]S(Cl)(=O)=O.O[C:7]1[C:12]([CH3:13])=[C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])[CH:10]=[CH:9][N:8]=1.C(=O)([O-])O.[Na+].[SH:26][C:27]1[NH:31][C:30]2[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=2[N:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C(O)C.C(N(CC)CC)C>[CH3:20][O:19][CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:1][S:26][C:27]2[NH:31][C:30]3[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=3[N:28]=2)[C:12]=1[CH3:13]

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 178495077HCID 178495077, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 15166285HCID 15166285, compoundYield 31.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

611 mg of triethylamine and 686 mg of methanesulfonyl chloride were added to a solution of 0.84 g of crude 2-hydroxy-4-(4-methoxybutoxy)-3-methylpyridine in 30 ml of dichloromethane at -20° C. under stirring and dehumidifying to obtain a mixture. This mixture was gradually brought to a room temperature, followed by the addition of a saturated aqueous solution of sodium hydrogencarbonate. The obtained mixture was stirred for 30 minutes and extracted with chloroform. The extract was dried over magnesium sulfate and distilled under a reduced pressure to remove the chloroform. Thus, a red oil was obtained. 560 mg of 2-mercapto-1H-benzimidazole and 30 ml of ethanol were added to this oil. The obtained mixture was stirred at a room temperature for 30 minutes, made basic with a 2N aqueous solution of sodium carbonate and extracted with chloroform. The extract was dried over magnesium sulfate and distilled under a reduced pressure to remove the chloroform. The obtained residue was chromatographed over a silica gel column and eluted with ethyl acetate/n-hexane to obtain 0.42 g of an oil.

Workup

  1. customto obtain a mixture
  2. customwas gradually brought to a room temperature
  3. stirringThe obtained mixture was stirred for 30 minutes
  4. extractionextracted with chloroform
  5. dry with materialThe extract was dried over magnesium sulfate
  6. distillationdistilled under a reduced pressure
  7. customto remove the chloroform
  8. customThus, a red oil was obtained
  9. stirringThe obtained mixture was stirred at a room temperature for 30 minutes
  10. extractionextracted with chloroform
  11. dry with materialThe extract was dried over magnesium sulfate
  12. distillationdistilled under a reduced pressure
  13. customto remove the chloroform
  14. customThe obtained residue was chromatographed over a silica gel column
  15. washeluted with ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-393b0ebc3a364fe6a516af4d1ccb018f
Source dataset
uspto-grants-1998_11
Patent number
US05840910

Reaction notes

Loading…