Pyridine → HCID 53708870, compound

HRID 1492315Notes

Reaction equation

HRID 1492315 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][C:4]1([CH3:9])[OH:8].N1C=CC=CC=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:9][C:4]1([OH:8])[CH2:5][CH2:6][CH2:7][CH:3]1[CH2:2][O:1][S:22]([C:19]1[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=1)(=[O:24])=[O:23]

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 53644243HCID 53644243, compound

Product 1

HCID 53708870HCID 53708870, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 7a (1.78 g, crude), pyridine (5.5 mL, 68.0 mmol) and 4-dimethylaminopyridine (0.17 g, 1.37 mmol) in CH2Cl2 (40 mL) was added p-toluenesulfonyl chloride (3.13 g, 16.4 mmol) in one portion, and the mixture was left to stand at 4° C. overnight. The mixture was stirred at ambient temperature for 100 min. To the mixture was added ice and the mixture was stirred at ambient temperature and the organic layer was separated. The aqueous layer was extracted with EtOAc and ,he combined organic layers were washed with water, CuSO4 solution, water, NaHCO3 solution and NaCl solution, and dried over Na2SO4. Filtration and concentration gave 3.86 g of 8a, which was used in the next reaction without further purification.

Workup

  1. waitthe mixture was left
  2. additionTo the mixture was added ice
  3. stirringthe mixture was stirred at ambient temperature
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with EtOAc
  6. washwere washed with water, CuSO4 solution, water, NaHCO3 solution and NaCl solution
  7. dry with materialdried over Na2SO4
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-0afc7640687a4e398ec046394687fc71
Source dataset
uspto-grants-1994_12
Patent number
US05373004

Reaction notes

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