Hydrochloric Acid → HCID 18950744, compound

HRID 1492563Notes

Reaction equation

HRID 1492563 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH2:13][CH2:14][NH2:15])=[CH:7][CH:6]=1.C(N(CC)CC)C.Cl[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36](Cl)(=[O:38])=[O:37].[ClH:40]>C(Cl)Cl.O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH:12]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH2:13][CH2:14][NH:15][S:36]([C:31]2[CH:32]=[CH:33][C:34]([Cl:40])=[CH:35][CH:30]=2)(=[O:38])=[O:37])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 761872-Chlorobenzenesulfonyl chlorideHCID 18950716HCID 18950716, compound

Product 1

HCID 18950744HCID 18950744, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To the solution of 0.72 g of 4-(4-methoxymethyloxyphenyl)-3-(3-pyridyl)butylamine and 0.27 g of triethylamine in methylene chloride, after cooling at 0° C., was added 0.51 g of chlorobenzene sulfonylchloride, and stirred at room temperature for five hours. To the reaction mixture was added water which was then adjusted to weak acidity with 2N hydrogen chloride, and the organic phase was separated which was then extracted from aqueous phase with methylene chloride. The combined organic phases were washed in saturated aqueous sodium chloride solution, and dried over magnesium sulfate, to distill off the solvent. The obtained residue was subjected to chromatography on a silica gel column, and from a fraction eluted with methanol-methylene chloride (5:95 v/v) was obtained 1.02 g of N-[4- (4-methoxymethyloxyphenyl)-3-(3-pyridyl)butyl]-4-chlorobenzenesulfonamide.

Workup

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

Sources & evidence

ORD record
ord-cf22b0b3dfe046b3a439189fae10e10c
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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