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Sodium Carbonate → HCID 19752321, compound

HRID 1885308
Notes
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Reaction equation

HRID 1885308 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][N:8]=1)=[O:6].[Cl:16][C:17]1[CH:31]=[CH:30][C:20]2[C:21]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[N:22][O:23][C:19]=2[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN1CCCC1=O.O>[Cl:16][C:17]1[CH:31]=[CH:30][C:20]2[C:21]([N:24]3[CH2:25][CH2:26][CH:27]([CH2:2][CH2:3][NH:4][C:5]([C:7]4[C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=5[S:9][N:8]=4)=[O:6])[CH2:28][CH2:29]3)=[N:22][O:23][C:19]=2[CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10263700HCID 10263700, compoundHCID 19752294HCID 19752294, compound

Product 1

HCID 19752321HCID 19752321, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 13387
N-methyl-2-pyrrolidone
Solvent

Conditions

Temperature
180 °C

Procedure

A mixture of N-(2-chloroethyl)-1,2-benzisothiazole-3-carboxamide (2.9 g) and 1-(6-chloro-1,2-benzisoxazol-3-yl)piperidine (3.48 g) in dry N-methylpyrrolidinone (125 ml) was heated to 180° C., with stirring, under nitrogen. After 5 hr, the reaction mixture was allowed to cool to room temperature, diluted with water, basified with saturated aqueous sodium carbonate solution, and extracted with ethyl acetate. The organic phase was washed with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was chromatographed on silica using ether as the eluent. The appropriate fractions were collected and evaporated. The residue was triturated with dichloromethane/ether to give 2.38 g (44.6%) of product, mp 132°-134° C.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was chromatographed on silica
  8. customThe appropriate fractions were collected
  9. customevaporated
  10. customThe residue was triturated with dichloromethane/ether

Sources & evidence

ORD record
ord-7b5ba688ae964c8480432dc133f235d1
Source dataset
uspto-grants-1992_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05143923

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes