Piperazine → 2-[2-Ethoxy-5-(1-piperazinylsulphonyl)pheny]-8-methylquinazolin-4(3H)-one

HRID 374769Notes

Reaction equation

HRID 374769 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[NH:19][C:18](=[O:20])[C:17]2[C:12](=[C:13]([CH3:21])[CH:14]=[CH:15][CH:16]=2)[N:11]=1)[CH3:2].Cl[S:23]([OH:26])(=O)=[O:24].S(Cl)(Cl)(=O)=O.[NH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:23]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)(=[O:26])=[O:24])=[CH:6][C:5]=1[C:10]1[NH:19][C:18](=[O:20])[C:17]2[C:12](=[C:13]([CH3:21])[CH:14]=[CH:15][CH:16]=2)[N:11]=1)[CH3:2]

Participants

7

Reactant 5

HCID 4837PiperazineHCID 10340Sodium CarbonateHCID 24638Chlorosulfonic acidHCID 24648Sulfuryl chlorideHCID 1357149122-(2-Ethoxyphenyl)-8-methylquinazolin-4(3H)-one

Product 1

HCID 1363755652-[2-Ethoxy-5-(1-piperazinylsulphonyl)pheny]-8-methylquinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-Ethoxyphenyl)-8-methylquinazolin-4(3H)-one (Preparation 4; 2.1 g, 0.0071 mol) was added portionwise to stirred chlorosulfonic acid (15 ml) under a nitrogen atmosphere at 0° C. After 18 hours, the mixture was cautiously added dropwise to stirred ice/water (100 g) and the resulting mixture extracted with dichloromethane-methanol (9:1, 10×100 ml). The organic extracts were combined, dried (MgS4) and evaporated under vacuum. A quantity (1.0 g) of the crude sulphonyl chloride was then added portionwise to a stirred solution of piperazine (2.1 g, 0.0244 mol) in ethanol (30 ml) at room temperature under a nitrogen atmosphere. After 18 hours the mixture was poured into stirred saturated aqueous sodium carbonate solution (100 ml) and the resulting mixture extracted with dichloromethane-methanol (9:1, 10×100 ml). The organic extracts were combined, dried (MgS4) and evaporated under vacuum to give the title compound, which crystallized from ethanol as a colorless solid (0.8 g, 71%), m.p. 163°-165 ° C. Found: C,56.76; H,5.72; N,11.77. C21H4N4O5S; 0.75 C2H5OH requires C,56.41; H,6.00; N,11.70%.

Workup

  1. additionthe mixture was cautiously added dropwise
  2. extractionthe resulting mixture extracted with dichloromethane-methanol (9:1, 10×100 ml)
  3. customdried (MgS4)
  4. customevaporated under vacuum
  5. additionAfter 18 hours the mixture was poured
  6. extractionthe resulting mixture extracted with dichloromethane-methanol (9:1, 10×100 ml)
  7. customdried (MgS4)
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-1f67416743b94b5eb81092a9e88436be
Source dataset
uspto-grants-1996_01
Patent number
US05482941

Reaction notes

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