Dichloromethane → HCID 15290698, compound

HRID 1720307Notes

Reaction equation

HRID 1720307 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].ClCCl.[CH2:12]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[NH:31][C:30](=[O:35])[CH:29]=[CH:28]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(N(CC)CC)C>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([N:19]([CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[NH:31][C:30](=[O:35])[CH:29]=[CH:28]2)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 154103-Chloropropanesulphonyl chlorideHCID 22923678HCID 22923678, compound

Product 1

HCID 15290698HCID 15290698, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

6.6 ml of 3-chloropropanesulfonyl chloride was dropwise added, at 0° C., to a dichloromethane solution containing 8 g of 6-(4-benzylaminobutoxy)carbostyril and 7.6 ml of triethylamine. The mixture was stirred at room temperature for 1 day. The reaction mixture was washed with 10% hydrochloric acid and water in this order and dried with magnesium sulfate. The solvent was removed by distillation. The resulting residue was dissolved in 30 ml of dioxane. To the solution was added 10 ml of a 10% potassium hydroxide solution, followed by stirring at room temperature for 30 minutes. The reaction mixture was neutralized with 10% hydrochloric acid, followed by extraction with chloroform. The extract was dried with magnesium sulfate. The solvent was removed by distillation. The resulting residue was crystallized from diethyl ether to obtain 7.3 g of 6-{4-[N-(3-chloropropylsulfonyl)-N-benzylamino]butoxy}carbostyril.

Workup

  1. washThe reaction mixture was washed with 10% hydrochloric acid and water in this order
  2. dry with materialdried with magnesium sulfate
  3. customThe solvent was removed by distillation
  4. dissolutionThe resulting residue was dissolved in 30 ml of dioxane
  5. additionTo the solution was added 10 ml of a 10% potassium hydroxide solution
  6. stirringby stirring at room temperature for 30 minutes
  7. extractionfollowed by extraction with chloroform
  8. dry with materialThe extract was dried with magnesium sulfate
  9. customThe solvent was removed by distillation
  10. customThe resulting residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-b8355eb424b0456bbe76f70a266c3931
Source dataset
uspto-grants-1996_04
Patent number
US05506239

Reaction notes

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