Hydrochloric Acid → HCID 15790190, compound

HRID 1080894Notes

Reaction equation

HRID 1080894 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.[CH3:23][S:24](Cl)(=[O:26])=[O:25].Cl>O.CCCCCC.O1CCCC1>[CH2:1]([S:8][C:9]1[N:10]=[C:11]([N:15]([CH2:16][CH3:17])[S:24]([CH3:23])(=[O:26])=[O:25])[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 31297Methanesulfonyl chlorideHCID 15790198HCID 15790198, compoundHCID 178418339Butyllithium

Product 1

HCID 15790190HCID 15790190, compoundYield 42.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a mixture of 6 g of 2-benzylthio-6-ethylaminopyridine and 60 ml of tetrahydrofuran was added dropwise 17.3 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 3.4 g of methysulfonyl 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 3.4 g of N-(6-benzylthiopyridine-2-yl)-N-ethylmethylsulfonamide as an orange crystal.

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-8fc1e427774f4f54a29f7f920b763055
Source dataset
uspto-grants-1996_12
Patent number
US05583231

Reaction notes

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