Sodium Carbonate → 1-[4-(7-Chloro-4-quinolinylamino)benzenesulphonyl]-4-(4-fluorobenzoyl)piperazine

HRID 568896Notes

Reaction equation

HRID 568896 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.Cl.[F:25][C:26]1[CH:39]=[CH:38][C:29]([C:30]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[O:31])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.O>[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([S:20]([N:35]4[CH2:34][CH2:33][N:32]([C:30](=[O:31])[C:29]5[CH:28]=[CH:27][C:26]([F:25])=[CH:39][CH:38]=5)[CH2:37][CH2:36]4)(=[O:22])=[O:21])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 201495884-(7-Chloro-4-quinolinylamino)benzenesulphonyl chloride hydrochlorideHCID 20149590(4-Fluorophenyl)(piperazin-1-yl)methanone hydrochloride

Product 1

HCID 136083001-[4-(7-Chloro-4-quinolinylamino)benzenesulphonyl]-4-(4-fluorobenzoyl)piperazineYield 5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

4-(7-Chloro-4-quinolinylamino)benzenesulphonyl chloride hydrochloride (7.8 g, 0.02 mol) was added portion-wise with stirring to a cold mixture of 1-(4-fluorobenzoyl) piperazine hydrochloride (4.9 g, 0.02 mol) in chloroform (250 ml) and sodium carbonate (24.4 g) in water (250 ml). The cooling bath was removed and the mixture was allowed to warm to room temperature. After 1 hour the chloroform layer was separated and dried (MgSO4). The solvent was removed by evaporation to give a brown gum. Crystallisation from ethanol gave the pure title compound (0.53 g), m.p. 235°-237° C.

Workup

  1. customThe cooling bath was removed
  2. customAfter 1 hour the chloroform layer was separated
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed by evaporation
  5. customto give a brown gum
  6. customCrystallisation from ethanol

Sources & evidence

ORD record
ord-1e8bc2f124ee4488a954bcb07d8efae4
Source dataset
uspto-grants-1988_03
Patent number
US04730047

Reaction notes

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