4-Methoxybenzenesulfonyl chloride → HCID 53964606, compound

HRID 1459673Notes

Reaction equation

HRID 1459673 reaction equation
[NH2:1][C:2]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1.O1CCCC1>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([NH:1][C:2]2[C:15]3[NH:14][C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[S:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)(=[O:26])=[O:25])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 15556090HCID 15556090, compound

Product 1

HCID 53964606HCID 53964606, compoundYield 59.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

107 mg (0.5 mmol) of 1-amino-10H-phenothiazine was dissolved in 4 ml of pyridine. Then 2 ml of a solution of 115 mg (0.55 mmol) of 4-methoxybenzenesulfonyl chloride in tetrahydrofuran was added thereto under stirring at room temperature. After stirring at room temperature overnight, the reaction mixture was concentrated. Then ethyl acetate and water were added to the residue and the organic layer was separated, washed with water and dried over magnesium sulfate. After concentrating, the residue was purified by silica gel column chromatography and recrystallized from ethanol. Thus 115 mg of the title compound was obtained.

Workup

  1. stirringAfter stirring at room temperature overnight
  2. concentrationthe reaction mixture was concentrated
  3. additionThen ethyl acetate and water were added to the residue
  4. customthe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationAfter concentrating
  8. customthe residue was purified by silica gel column chromatography
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-9ad11917478742449226cef964354e93
Source dataset
uspto-grants-1998_12
Patent number
US05854274

Reaction notes

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