Acetyl chloride → HCID 13544866, compound

HRID 237019Notes

Reaction equation

HRID 237019 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(Cl)(=O)C.Cl[C:30]1[C:39]2[C:34](=[CH:35][C:36]([C:40]([F:43])([F:42])[F:41])=[CH:37][CH:38]=2)[N:33]=[CH:32][CH:31]=1>C(O)C>[CH3:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:14]1[CH2:15][CH2:16][N:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:30]3[C:39]4[C:34](=[CH:35][C:36]([C:40]([F:43])([F:41])[F:42])=[CH:37][CH:38]=4)[N:33]=[CH:32][CH:31]=3)=[CH:3][CH:4]=2)(=[O:9])=[O:10])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 676684-Chloro-7-(trifluoromethyl)quinolineHCID 6494482HCID 6494482, compound

Product 1

HCID 13544866HCID 13544866, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 1.73 g (0.00498 n) of 1-[(p-aminophenyl)sulfonyl]-4-(o-methoxyphenyl)piperazine in absolute ethanol is added 0.35 ml acetyl chloride in 5 ml ethanol (source of hydrogen chloride). After stirring for 5 minutes, 1.15 g (0.00498 m) of 4-chloro-7-trifluoromethylquinoline is added. The reaction mixture is stirred at reflux for 3 hours and at room temperature overnight. The solvent is then removed in vacuo and the residue is extracted with methylene chloride/aqueous sodium bicarbonate. The organic layer is filtered through anhydrous sodium sulfate and taken to dryness and the product mixture is chromatographed on silica gel, once with 4% methanol: 96% methylene chloride as eluant, and a second time with methylene chloride as the eluant. Crystallization from methylene chloride/Skelly-solve® B hexanes gives 1.61 g (61%) of 1-(2-methoxyphenyl)-4-[[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]phenyl]sulfonyl]piperazine of melting point 146°-148° C.

Workup

  1. stirringThe reaction mixture is stirred
  2. customThe solvent is then removed in vacuo
  3. extractionthe residue is extracted with methylene chloride/aqueous sodium bicarbonate
  4. filtrationThe organic layer is filtered through anhydrous sodium sulfate
  5. customthe product mixture is chromatographed on silica gel, once with 4% methanol
  6. customCrystallization from methylene chloride/Skelly-solve® B hexanes

Sources & evidence

ORD record
ord-fca63f23c6f9427c9ab2a341f7b8a37b
Source dataset
uspto-grants-1979_06
Patent number
US04159331

Reaction notes

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