Potassium Carbonate → HCID 14720320, compound

HRID 2351988Notes

Reaction equation

HRID 2351988 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:23][CH2:24][S:25](Cl)(=[O:27])=[O:26].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[S:25]([CH2:24][Cl:23])(=[O:27])=[O:26])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 77054(Chloromethyl)sulfonyl chlorideHCID 516892Sodium BicarbonateHCID 14720319HCID 14720319, compound

Product 1

HCID 14720320HCID 14720320, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 3.4 g. portion of 3-(4-methylthiophenylaminomethyl)pyridine was dissolved in 25 ml. of dichloromethane, and 4.1 g. of potassium carbonate and 4.5 g. of chloromethanesulfonyl chloride were added. The mixture was stirred at ambient temperature for 4 days, and then 20 ml. of aqueous sodium bicarbonate was added. The mixture was extracted with 15 ml. of dichloromethane, and the organic phase was washed with aqueous sodium bicarbonate, dried and evaporated to an oil. The oil was dissolved in dichloromethane and chromatographed on silica gel, eluting with dichloromethane. Combination of the product-containing fractions gave 1.6 g. of the desired product.

Workup

  1. extractionThe mixture was extracted with 15 ml
  2. washof dichloromethane, and the organic phase was washed with aqueous sodium bicarbonate
  3. customdried
  4. customevaporated to an oil
  5. dissolutionThe oil was dissolved in dichloromethane
  6. customchromatographed on silica gel
  7. washeluting with dichloromethane
  8. customCombination of the product-containing fractions gave 1.6 g

Sources & evidence

ORD record
ord-909b17b5589f42ba846af07c6f487378
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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