Potassium Carbonate → HCID 23666225, compound

HRID 486610Notes

Reaction equation

HRID 486610 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.Cl[S:28]([OH:31])(=[O:30])=[O:29].C(=O)([O-])[O-].[K+:36].[K+]>N1C=CC=CC=1>[S:28]([O-:31])([O:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1)(=[O:30])=[O:29].[K+:36]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24638Chlorosulfonic acidHCID 3035714N-[2-[(4-Hydroxyphenyl)amino]-3-pyridinyl]-4-methoxybenzenesulfonamide

Product 1

HCID 23666225HCID 23666225, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.0 g (5.38 mmol) of the compound of Example 6 was dissolved in 20 ml of pyridine. 800 mg (6.87 mmol) of chlorosulfonic acid (95%) was added dropwise thereto at -15° to -10° C. The temperature was slowly elevated to room temperature and the mixture was stirred for 3 days. A 1N aqueous potassium carbonate solution was added to the reaction mixture to adjust the pH to 8 to 9. The solvent was distilled off under reduced pressure. Water and ethyl acetate were added to the residue and an aqueous layer thus formed was separated, concentrated, purified by silica gel column chromatography and precipitated with methanol/dichloromethane to obtain 1.58 g of the title compound.

Workup

  1. customat -15° to -10° C
  2. customwas slowly elevated to room temperature
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionWater and ethyl acetate were added to the residue
  5. customan aqueous layer thus formed
  6. customwas separated
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography
  9. customprecipitated with methanol/dichloromethane

Sources & evidence

ORD record
ord-07c664627c514fcd9ea2dcaf1bfd2c45
Source dataset
uspto-grants-1994_03
Patent number
US05292758

Reaction notes

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