4-Methoxybenzenesulfonyl chloride → HCID 86746452, compound

HRID 1645886Notes

Reaction equation

HRID 1645886 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH2:13][C:14]1[C:30]([CH3:31])=[CH:29][C:17]([O:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:28])([CH3:27])[C:23]([O:25][CH3:26])=[O:24])=[C:16]([CH3:32])[CH:15]=1.C(N(CC)CC)C>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:13][C:14]2[C:30]([CH3:31])=[CH:29][C:17]([O:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:27])([CH3:28])[C:23]([O:25][CH3:26])=[O:24])=[C:16]([CH3:32])[CH:15]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 15068117HCID 15068117, compound

Product 1

HCID 86746452HCID 86746452, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.2 g (12.5 mmol) of para-methoxybenzenesulfonyl chloride in 10 mL of tetrahydrofuran is added over 10 minutes at 0° C. to a solution of 3.5 g (12.5 mmol) of 5-(4-amino-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid, methyl ester as the free base (Example 2) and 2.5 g (2×12.5 mmol) of triethylamine in 40 mL of tetrahydrofuran. The ice bath is removed and the solution is permitted to stir at ambient temperature for 24 hours. The triethylammonium chloride is removed by filtration, the solvent is removed; the residue is taken up in diethyl ether, and the solution washed with 2×25 mL of 2N hydrochloric acid solution, brine, dried (magnesium sulfate), and evaporated leaving 5.0 g of a colored oil which crystallizes on standing. Recrystallization from 35 mL of isopropyl ether in the presence of charcoal affords 3.3 g of the title compound as off-white crystals; mp 90°-92° C.

Workup

  1. customThe ice bath is removed
  2. customThe triethylammonium chloride is removed by filtration
  3. customthe solvent is removed
  4. washthe solution washed with 2×25 mL of 2N hydrochloric acid solution, brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated

Sources & evidence

ORD record
ord-a5f10f10b8cc41efbde4d95705d07fd6
Source dataset
uspto-grants-1993_01
Patent number
US05177106

Reaction notes

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