Potassium Carbonate → HCID 19844834, compound

HRID 2351984Notes

Reaction equation

HRID 2351984 reaction equation
[CH2:1]([NH:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH2:1]([N:13]([CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[S:28]([CH3:27])(=[O:30])=[O:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 19844883HCID 19844883, compound

Product 1

HCID 19844834HCID 19844834, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 4.1 g. portion of 3-dodecylaminomethylpyridine was dissolved in 15 ml. of dichloromethane, and 2.7 g. of potassium carbonate and 1.6 ml. of methanesulfonyl chloride were added. The mixture was stirred for 3 days at ambient temperature, and was then diluted with dichloromethane and extracted with water. The organic layer was dried and evaporated to an oil, which was dissolved in dichloromethane and chromatographed over silica gel, eluting with dichloromethane. The product-containing fractions were combined and evaporated to obtain 3.5 g. of oil which crystallized on standing, and was triturated with cold petroleum ether and diethyl ether. The solids were dried to obtain 3.2 g. of the desired product, m.p. 43°-44°.

Workup

  1. extractionextracted with water
  2. customThe organic layer was dried
  3. customevaporated to an oil, which
  4. dissolutionwas dissolved in dichloromethane
  5. customchromatographed over silica gel
  6. washeluting with dichloromethane
  7. customevaporated
  8. customto obtain 3.5 g
  9. customof oil which crystallized
  10. customwas triturated with cold petroleum ether and diethyl ether
  11. customThe solids were dried
  12. customto obtain 3.2 g

Sources & evidence

ORD record
ord-a27ed58764ae4601ad5a94d19271903c
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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