Pyridine → HCID 86752143, compound

HRID 863484Notes

Reaction equation

HRID 863484 reaction equation
[OH:1][CH:2]1[CH2:11][C:10]2[C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[CH3:16][S:17](Cl)(=[O:19])=[O:18].N1C=CC=CC=1>C(Cl)Cl>[C:13]([NH:12][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH2:11][CH:2]([O:1][S:17]([CH3:16])(=[O:19])=[O:18])[CH2:3][CH2:4]2)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 19696265HCID 19696265, compound

Product 1

HCID 86752143HCID 86752143, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)-acetamide (5 g, 24 mmol), methylsulfonylchloride (6.9 g, 60 mmol) and pyridine (4.7 g, 60 mmol) in methylene chloride (100 mL) was heated at reflux for 8 h. The mixture was then cooled and washed with water. The organic layer was dried over magnesium sulfate, filtered and evaporated. The resulting solid was washed with diethyl ether and dried (3.8 g, 51% yield) without further purification.

Workup

  1. temperatureat reflux for 8 h
  2. temperatureThe mixture was then cooled
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. washThe resulting solid was washed with diethyl ether
  8. customdried (3.8 g, 51% yield)
  9. customwithout further purification

Sources & evidence

ORD record
ord-d3555e3581c34ad7b77e7f2d89a00cdb
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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