Water → 4-Chlorobenzenesulfonamide

HRID 1492550Notes

Reaction equation

HRID 1492550 reaction equation
OC1C=CC(CC(C2C=NC=CC=2)C[NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=CC=1.C(N(CC)CC)C.C(Cl)(=O)OCC.O>C(Cl)Cl>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([NH2:11])(=[O:13])=[O:14])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 18950670HCID 18950670, compound

Product 1

HCID 668244-Chlorobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-[3-(4-hydroxyphenyl)-2-(3-pyridyl)propyl]-4-chlorobenzenesulfonamide (54.5 mg) and 15.1 mg of triethylamine were dissolved in 3 ml of methylene chloride, followed by addition of 16.2 mg of ethyl chlorocarbonate dissolved in 1 ml of methylene chloride, and stirred at room temperature for 15 hours. To the reaction mixture was added water, and the organic phase was separated which was then extracted with methylene chloride. The organic phases were combined and washed in water, followed by drying 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 47.4 mg of N-[3-(4-ethoxycarbonylphenyl)-2-(3-pyridyl)}propyl]-4-chlorobenzene sulfonamide. The spectrometric data supports the structure of [35] as follows.

Workup

  1. customthe organic phase was separated which
  2. extractionwas then extracted with methylene chloride
  3. washwashed in water
  4. dry with materialby drying 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-8110d2bb83b04f119c5e56ff4c58fc5d
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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