Sodium Iodide → HCID 13656627, compound

HRID 579751Notes

Reaction equation

HRID 579751 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][S:11](=[O:20])(=[O:19])[C:10]2[CH:21]=[CH:22][C:23]([CH3:25])=[CH:24][C:9]1=2)=[O:6].[F:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[CH:29][CH:28]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:26][C:27]1[CH:28]=[CH:29][C:30]([N:33]2[CH2:38][CH2:37][N:36]([CH2:2][CH2:3][CH2:4][C:5]([NH:7][CH:8]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[CH2:12][S:11](=[O:20])(=[O:19])[C:10]4[CH:21]=[CH:22][C:23]([CH3:25])=[CH:24][C:9]3=4)=[O:6])[CH2:35][CH2:34]2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 752601-(4-Fluorophenyl)piperazineHCID 13656625HCID 13656625, compound

Product 1

HCID 13656627HCID 13656627, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2.0 g of 11-(4-chlorobutyrylamino)-2-methyl-6,11-dihydrodibenzo[b,e]thiepin-5,5-dioxide, 2.0 g of 1-(4-fluorophenyl)piperazine, 2.0 g of sodium iodide and 20 ml of dimethylformamide is stirred at 100° C. for one hour. After the reaction mixture is cooled to room temperature, 100 ml of 10% aqueous potassium carbonate solution is added and the solution is extracted with three 300-ml portions of chloroform. The combined extracts are washed successively with water and saturated aqueous sodium chloride solution, and dried over magnesium sulfate, and the chloroform is distilled off. The residue is recrystallized from chloroform-diethyl ether to give 2.1 g of the title compound, m.p. 163°-165° C.

Workup

  1. temperatureAfter the reaction mixture is cooled to room temperature
  2. extractionthe solution is extracted with three 300-ml portions of chloroform
  3. washThe combined extracts are washed successively with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. distillationthe chloroform is distilled off
  6. customThe residue is recrystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-e9772d5fd9324c789271fa514b2bd25a
Source dataset
uspto-grants-1988_06
Patent number
US04749703

Reaction notes

Loading…