Dimethyl Sulfoxide → HCID 13236318, compound

HRID 1649216Notes

Reaction equation

HRID 1649216 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.CS(C)=O.[N+:29]([C:32]1[CH:33]=[C:34]([CH:38]=[C:39]([N+:41]([O-:43])=[O:42])[CH:40]=1)[C:35](Cl)=[O:36])([O-:31])=[O:30]>O>[N+:29]([C:32]1[CH:33]=[C:34]([CH:38]=[C:39]([N+:41]([O-:43])=[O:42])[CH:40]=1)[C:35]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]3)[CH2:2][CH2:3]1)=[O:36])([O-:31])=[O:30]

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 74323,5-Dinitrobenzoyl chlorideHCID 8471TriethylamineHCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 13236318HCID 13236318, compoundYield 6.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-(1-Piperazinyl)-3,4-dihydrocarbostyril (2.6 g) and 2.34 ml of triethylamine was added to 40 ml of dimethyl sulfoxide and the mixture was stirred at room temperature while slowly adding dropwise 10 ml of dimethyl sulfoxide solution containing 3.3 g of 3,5-dinitrobenzoyl chloride. After completion of addition the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into a large amount of water and extracted with chloroform. The extract was washed with saturated sodium hydrogencarbonate solution and subsequently with water and dried over anhydrous sodium sulfate, chloroform was distilled off and residual crystals were recrystallized from methanol-chloroform to give 0.3 g of 6-[4-(3,5-dinitrobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 262°-264° C., reddish black needles.

Workup

  1. additionAfter completion of addition the reaction mixture
  2. stirringwas stirred at room temperature for 30 minutes
  3. extractionextracted with chloroform
  4. washThe extract was washed with saturated sodium hydrogencarbonate solution and subsequently with water
  5. dry with materialdried over anhydrous sodium sulfate, chloroform
  6. distillationwas distilled off
  7. customresidual crystals were recrystallized from methanol-chloroform

Sources & evidence

ORD record
ord-41ea08d263294481b8db9bb0cbaa3e44
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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