Sulfuric Acid → HCID 54474718, compound

HRID 1657609Notes

Reaction equation

HRID 1657609 reaction equation
S(=O)(=O)(O)O.C([O:9][C:10]1[CH:23]=[CH:22][C:21]2[S:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[S:24](=[O:29])(=[O:28])[N:25]([CH3:27])[CH3:26])[N:13]([CH2:30][CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][CH:36]([CH2:39][CH2:40][OH:41])[CH2:35][CH2:34]3)[C:12]=2[CH:11]=1)(C)C.[OH-].[Na+]>C(Cl)(Cl)Cl>[OH:9][C:10]1[CH:23]=[CH:22][C:21]2[S:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[S:24](=[O:28])(=[O:29])[N:25]([CH3:27])[CH3:26])[N:13]([CH2:30][CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][CH:36]([CH2:39][CH2:40][OH:41])[CH2:35][CH2:34]3)[C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 54222110HCID 54222110, compound

Product 1

HCID 54474718HCID 54474718, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
5 °C

Procedure

Concentrated sulphuric acid (109 g.) cooled to 5°C. is added over the course of 30 seconds to a solution, kept at 5°C, of 2-isopropoxy-6-dimethylsulphamoyl-10-[3-(4-hydroxyethylpiperidino)propyl]-phenothiazine (10.9 g.) in anhydrous chloroform (150 cc.). After stirring for 30 seconds at 5°C., the reaction mixture is poured onto crushed ice (150 g.). The pH of the solution is brought to 7.5 by addition of sodium hydroxide solution (d = 1.33), whilst cooling, and extraction is effected using chloroform (total 350 cc.). The chloroform solution is dried over anhydrous sodium sulphate (5 g.), the solvent evaporated under reduced pressure and the product obtained dried under reduced pressure (0.05 mm. Hg) at 20°C. The resulting amorphous product (5.1 g.) is dissolved in boiling acetonitrile (35 cc.). After cooling, the crystals which have formed are filtered off, washed with acetonitrile (5 cc.) and dried at 50°C. under reduced pressure (0.05 mm. Hg) for 20 hours. 2-Hydroxy-6-dimethylsulphamoyl-10-[3-(4-hydroxyethylpiperidino)propyl]phenothiazine (3.9 g.), melting at 163°-165°C., is obtained.

Workup

  1. additionis added over the course of 30 seconds to a solution
  2. additionthe reaction mixture is poured
  3. temperaturewhilst cooling
  4. extractionextraction
  5. dry with materialThe chloroform solution is dried over anhydrous sodium sulphate (5 g.)
  6. customthe solvent evaporated under reduced pressure
  7. customthe product obtained
  8. customdried under reduced pressure (0.05 mm. Hg) at 20°C
  9. dissolutionThe resulting amorphous product (5.1 g.) is dissolved
  10. temperatureAfter cooling
  11. customthe crystals which have formed
  12. filtrationare filtered off
  13. washwashed with acetonitrile (5 cc.)
  14. customdried at 50°C. under reduced pressure (0.05 mm. Hg) for 20 hours

Sources & evidence

ORD record
ord-338bfe896ef34a15ab5fcfd7be0ae7c7
Source dataset
uspto-grants-1976_06
Patent number
US03961055

Reaction notes

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