Hydrochloric Acid → HCID 15790199, compound

HRID 2209920Notes

Reaction equation

HRID 2209920 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH2:16][CH3:17])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH:23]([S:26](Cl)(=[O:28])=[O:27])([CH3:25])[CH3:24].Cl>O.CCCCCC.O1CCCC1>[CH2:1]([S:8][C:9]1[N:10]=[C:11]([N:15]([CH2:16][CH3:17])[S:26]([CH:23]([CH3:25])[CH3:24])(=[O:28])=[O:27])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 824082-Propanesulfonyl chlorideHCID 15790198HCID 15790198, compoundHCID 178418339Butyllithium

Product 1

HCID 15790199HCID 15790199, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a mixture of 3.16 g of the 2-benzylthio-6-ethylaminopyridine obtained in 1) above and 30 ml of tetrahydrofuran was added dropwise 9.4 ml of a 1.65 mol/l hexane solution of n-butyl lithium at -10° to 0° C. in a nitrogen stream. To the reaction mixture was added 1.84 g of isopropylsulfonyl chloride at 0° to 15° C., followed by reacting for 0.5 hour. After completion of the reaction, the reaction mixture was poured into water, made weakly acidic with hydrochloric acid, and extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/19 by volume) to obtain 0.77 g of N-(6-benzylthiopyridin-2-yl)-N-ethylisopropylsulfonamide as an oily substance.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with methylene chloride
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationfollowed by concentration under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/19 by volume)

Sources & evidence

ORD record
ord-483ee4f2b41b4affb0e64ec896946cb5
Source dataset
uspto-grants-1995_10
Patent number
US05457084

Reaction notes

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