Hydrochloric Acid → HCID 18799348, compound

HRID 1638067Notes

Reaction equation

HRID 1638067 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([N:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][S:8][C:4]=2[CH:3]=1.Br[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C([O-])([O-])=O.[K+].[K+].[ClH:31]>CCOCC.CCOC(C)=O.O>[ClH:31].[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([N:9]3[CH2:14][CH2:13][N:12]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:11][CH2:10]3)=[N:7][S:8][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 68320Ethyl 3-bromopropionateHCID 187993396-Fluoro-3-(1-piperazinyl)-1,2-benzisothiazole

Product 1

HCID 18799348HCID 18799348, compoundYield 6.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperazinyl)-1,2-benzisothiazole (6.0 g, 25 mmol), ethyl 3-bromopropionate (4.5 g, 25 mmol), K2CO3 (3.5 g) CH3CN (100 ml) was stirred and refluxed for 16 hours. The reaction was poured into H2O, and after extractive workup with EtOAc, 6.0 g of am orange oil was realized. The oil was dissolved in Et2O and ethereal HCl was added to precipitate 6.3 g of a white hydrochloride salt. The salt was recrystallized from CH3CN to yield 6.0 g (6.4%) of the desired compound. An analytical sample was obtained by recrystallization of a 1.0 g sample from EtOH-Et2O to yield 0.8 g of a white solid, m.p.=197-199° C.

Workup

  1. temperaturerefluxed for 16 hours
  2. customto precipitate 6.3 g of a white hydrochloride salt
  3. customThe salt was recrystallized from CH3CN

Sources & evidence

ORD record
ord-6dde11184f1e4532acdf1b5c1613b70a
Source dataset
uspto-grants-2000_03
Patent number
US06043240

Reaction notes

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