4-Methoxybenzenesulfonyl chloride → 4-[[4-Methoxybenzenesulfonyl]amino]-4-carbomethoxy-tetrahydrothiopyran

HRID 1720598Notes

Reaction equation

HRID 1720598 reaction equation
Cl.[NH2:2][C:3]1([C:9]([O:11][CH3:12])=[O:10])[CH2:8][CH2:7][S:6][CH2:5][CH2:4]1.C(N(CC)CC)C.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>C(Cl)Cl.O>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([S:28]([NH:2][C:3]2([C:9]([O:11][CH3:12])=[O:10])[CH2:4][CH2:5][S:6][CH2:7][CH2:8]2)(=[O:30])=[O:29])=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 22907152Methyl 4-aminothiane-4-carboxylate hydrochloride

Product 1

HCID 229070824-[[4-Methoxybenzenesulfonyl]amino]-4-carbomethoxy-tetrahydrothiopyran

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-4-carbomethoxy-tetrahydrothiopyran hydrochloride (3.1 g, 15.0 mmol) in methylene chloride (75 mL) containing triethylamine (3.5 g, 330.0 mmol) is added 4-methoxybenzenesulfonyl chloride (4.1 g, 20.0 mmol) at room temperature. The reaction mixture is stirred at room temperature for 18 hours. The mixture is diluted with water and the organic layer is removed. The aqueous layer is extracted with diethyl ether and the organic extracts are washed with brine, dried (MgSO4) and the solvent is evaporated. The product is purified by silica gel chromatography (50% ethylacetate/hexanes) to provide 4-[[4-methoxybenzenesulfonyl]amino]-4-carbomethoxy-tetrahydrothiopyran.

Workup

  1. customthe organic layer is removed
  2. extractionThe aqueous layer is extracted with diethyl ether
  3. washthe organic extracts are washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent is evaporated
  6. customThe product is purified by silica gel chromatography (50% ethylacetate/hexanes)

Sources & evidence

ORD record
ord-5d29c42325464e6b8986adedbd7e81c6
Source dataset
uspto-grants-1996_04
Patent number
US05506242

Reaction notes

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