Hydrochloric Acid → 4-(4-methoxy-benzenesulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine

HRID 1943678Notes

Reaction equation

HRID 1943678 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[N:8][CH:9]=[CH:10][C:2]1=2.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(N(CC)CC)C.Cl>ClCCl>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([S:19]([N:4]2[CH2:5][CH2:6][O:1][C:2]3[CH:10]=[CH:9][N:8]=[CH:7][C:3]2=3)(=[O:21])=[O:20])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazine

Product 1

HCID 669366164-(4-methoxy-benzenesulfonyl)-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazineYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 25 ml flask, 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (370 mg, 2.72 mmol) and 4-methoxy-benzenesulfonyl chloride (618 mg, 2.99 mmol) were dissolved in dichloromethane (10 ml). Triethylamine (0.45 ml, 3.23 mmol) was added thereto and then stirred at room temperature for 2 hours. After neutralizing with 1N hydrochloric acid solution, the mixture was extracted with dichloromethane, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of dichloromethane. The fractions containing the product were collected and evaporated to obtain pale-green solid (700 mg, 84.1%).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica eluting with a solvent of dichloromethane
  6. additionThe fractions containing the product
  7. customwere collected
  8. customevaporated

Sources & evidence

ORD record
ord-835305ff10ea40f8bbf1a261084a5621
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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