Methanesulfonic Acid → HCID 9850401, compound

HRID 1066712Notes

Reaction equation

HRID 1066712 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][C:26]=3[Cl:27])[NH:23][C:22](=[O:28])[CH2:21]4)[CH2:12][CH2:11]2)=[N:2]1.[Al].[CH3:30][S:31]([OH:34])(=[O:33])=[O:32]>O>[OH2:28].[OH2:32].[CH3:30][S:31]([OH:34])(=[O:33])=[O:32].[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][C:26]=3[Cl:27])[NH:23][C:22](=[O:28])[CH2:21]4)[CH2:14][CH2:15]2)=[N:2]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 60854ZiprasidoneHCID 5359268Aluminum

Product 1

HCID 9850401HCID 9850401, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
52.5 °C

Procedure

A slurry was produced by charging 25 g of 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one and 375 mL of water to a 500 mL, three-neck, round-bottom flask equipped with a heating mantle, an overhead mechanical stirrer, a condenser, and a temperature probe. The flask contents were protected from light with an aluminum foil cover. The slurry was heated to 50-55° C. while stirring. Methanesulfonic acid (5 mL) was added slowly through a dropping funnel to the reaction mixture. Thickening of the slurry and lightening of the slurry color were observed. The reaction was heated to reflux (about 100° C.) and allowed to stir for about one hour. The heat was removed to allow slow cooling of the reaction with stirring. The reaction solution was allowed to stir under ambient conditions for about one hour. The product was isolated on a Buchner funnel with a paper filter and the solids were allowed to dry under ambient conditions to a Karl Fischer value of about 6.2%. The yield was 32.11 g of product. The purity of the product, as determined by HPLC (conditions in Table 5), was 98.7%.

Workup

  1. customA slurry was produced
  2. customequipped with a heating mantle, an overhead mechanical stirrer, a condenser
  3. temperatureThe reaction was heated
  4. temperatureto reflux (about 100° C.)
  5. stirringto stir for about one hour
  6. customThe heat was removed
  7. temperatureto allow slow cooling of the reaction
  8. stirringwith stirring
  9. stirringto stir under ambient conditions for about one hour
  10. customThe product was isolated on a Buchner funnel with a paper
  11. filtrationfilter
  12. customto dry under ambient conditions to a Karl Fischer value of about 6.2%

Sources & evidence

ORD record
ord-c630f8eee2c64a8599869544589e000e
Source dataset
uspto-grants-2001_06
Patent number
US06245765B1

Reaction notes

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