Water → Sitalidone

HRID 231833

Reaction equation

HRID 231833 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[C:5]([OH:11])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2([OH:29])[N:26]([CH3:27])[C:25](=[O:28])[CH2:24][CH2:23]2)=[CH:18][C:17]=1[S:30](Cl)(=[O:32])=[O:31].C(N(CC)CC)C.O>C(OCC)(=O)C>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2([OH:29])[N:26]([CH3:27])[C:25](=[O:28])[CH2:24][CH2:23]2)=[CH:18][C:17]=1[S:30](=[O:32])(=[O:31])[NH:1][C:2]1[CH:3]=[C:4]([CH:12]([CH3:14])[CH3:13])[C:5]([OH:11])=[C:6]([CH:8]([CH3:9])[CH3:10])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8185384-Amino-2,6-diisopropylphenolHCID 142568045-(4-Chloro-3-chlorosulfonylphenyl)-5-hydroxy-1-methyl-2-pyrrolidone

Product 1

HCID 3086530Sitalidone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
50 °C

Procedure

A suspension of 29.1 g of 4-amino-2,6-diisopropylphenol in 450 ml of ethyl acetate is added in portions to a solution of 17.5 g of 5-(4-chloro-3-chlorosulfonylphenyl)-5-hydroxy-1-methyl-2-pyrrolidone and 22.7 g of triethylamine in 200 ml of ethyl acetate. The mixture is stirred at 50° C. for 3 hours, cooled, water is added, the organic phase is separated off, and the aqueous phase is extracted several times with ethyl acetate. The combined organic phases are washed with water and dried over sodium sulfate, and the solvent is distilled off. After addition of about 250 ml of methylene chloride to the amorphous red residue it is refluxed and crystallization is induced by scratching. The mixture is stirred at room temperature for 30 min, and the precipitate is filtered off and recrystallized from acetonitrile without prolonged standing. Colorless crystals of melting point 198°-200° C.

Workup

  1. temperaturecooled
  2. customthe organic phase is separated off
  3. extractionthe aqueous phase is extracted several times with ethyl acetate
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. distillationthe solvent is distilled off
  7. additionAfter addition of about 250 ml of methylene chloride to the amorphous red residue it
  8. temperatureis refluxed
  9. customcrystallization
  10. stirringThe mixture is stirred at room temperature for 30 min
  11. filtrationthe precipitate is filtered off
  12. customrecrystallized from acetonitrile without prolonged standing

Sources & evidence

ORD record
ord-47181b98a10e40aca7760517aa15a1ad
Source dataset
uspto-grants-1989_07
Patent number
US04849444

Linked notes

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