Chlorosulfonic acid → HCID 18707243, compound

HRID 1489246Notes

Reaction equation

HRID 1489246 reaction equation
Cl[S:2]([OH:5])(=[O:4])=[O:3].[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=3)[S:16][CH:17]=2)=[CH:9][CH:8]=1>N1C=CC=CC=1>[OH:5][S:2]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=3)[S:16][CH:17]=2)=[CH:9][CH:8]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 18707166HCID 18707166, compound

Product 1

HCID 18707243HCID 18707243, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

2 ml of chlorosulfonic acid was dropwise added to 40 ml of pyridine at room temperature. The mixture was stirred at 50° C. for 12 hours. Thereto was added 0.33 g of 4-(4-hydroxyphenyl-2-(3,4-dimethoxyphenyl)thiazole. The mixture was stirred at 50° C. for 6 hours and then at room temperature overnight. The reaction mixture was concentrated to dryness under reduced pressure. The residue was mixed with water and the resulting crystals were collected by filtration. The resulting 4-(4-hydroxysulfonyloxyphenyl)-2-(3,4-dimethoxyphenyl)thiazole pyridinium salt was suspended in 3 ml of methanol. Thereto was added 5 ml of a 0.1N aqueous potassium hydroxide solution. The mixture was stirred at room temperature overnight. The reaction mixture was concentrated. The residue was dissolved in water. The solution was treated with 0.5 g of an ion exchange resin (Dowex 50Wx8). The filtrate was concentrated to obtain 0.04 g of 4-(4-hydroxysulfonyloxyphenyl)-2-(3,4-dimethoxyphenyl)thiazole.

Workup

  1. stirringThe mixture was stirred at 50° C. for 6 hours
  2. customat room temperature
  3. customovernight
  4. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  5. additionThe residue was mixed with water
  6. filtrationthe resulting crystals were collected by filtration
  7. additionThereto was added 5 ml of a 0.1N aqueous potassium hydroxide solution
  8. stirringThe mixture was stirred at room temperature overnight
  9. concentrationThe reaction mixture was concentrated
  10. dissolutionThe residue was dissolved in water
  11. additionThe solution was treated with 0.5 g of an ion exchange resin (Dowex 50Wx8)
  12. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b68a574c16de41819c032130fc0e39e3
Source dataset
uspto-grants-1997_10
Patent number
US05677319

Reaction notes

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