Water → HCID 18950755, compound

HRID 1492547Notes

Reaction equation

HRID 1492547 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:13][NH2:14])=[CH:7][CH:6]=1.C(N(CC)CC)C.Cl[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[S:35](Cl)(=[O:37])=[O:36].O.C(Cl)[Cl:41]>>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH:12]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:13][NH:14][S:35]([C:30]2[CH:31]=[CH:32][C:33]([Cl:41])=[CH:34][CH:29]=2)(=[O:37])=[O:36])=[CH:9][CH:10]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 8471TriethylamineHCID 761872-Chlorobenzenesulfonyl chlorideHCID 18950754HCID 18950754, compound

Product 1

HCID 18950755HCID 18950755, compound

Procedure

To the solution of 4.98 g of 3-(4-methoxymethyloxyphenyl)-2-(3-pyridyl)propylamine and 100 ml of the solution of 2.22 g of triethylamine in methylene chloride was added 4.63 g of chlorobenzenesulfonyl chloride, and stirred at room temperature for four hours. The reaction mixture was poured into water, and the organic phase was separated which was then extracted with methylene chloride from aqueous phase. The combined organic phases were washed in saturated aqueous sodium chloride, and dried over magnesium sulfate, to distill off the solvent. The obtained residue was subjected to chromatography on a silica gel column, and from the fraction eluted with methanol-methylene chloride (5:95 v/v) was obtained 3.79 g of N-[3-(4-methoxymethyloxyphenyl)-2-(3-pyridyl)propyl]-4-chlorobenzene sulfonamide.

Workup

  1. customthe organic phase was separated which
  2. extractionwas then extracted with methylene chloride from aqueous phase
  3. washThe combined organic phases were washed in saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. distillationto distill off the solvent
  6. washfrom the fraction eluted with methanol-methylene chloride (5:95 v/v)

Sources & evidence

ORD record
ord-241df38cc1894f559ec9a878645efcbf
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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