Sodium Hydroxide → HCID 19822323, compound

HRID 1030207Notes

Reaction equation

HRID 1030207 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl[C:15]([CH3:19])([CH3:18])[C:16]#[CH:17].[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[CH3:12][N:11]([CH3:13])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([O:1][C:15]([CH3:19])([CH3:18])[C:16]#[CH:17])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 706791-Butyne, 3-chloro-3-methyl-HCID 84760Benzenesulfonamide, 4-hydroxy-N,N-dimethyl-

Product 1

HCID 19822323HCID 19822323, compoundYield 37.1%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A two-phase mixture of 4-hydroxy-N,N-dimethyl-benzenesulfonamide (13 g), 3-chloro-3-methyl-1-butyne (33 g), tetra-n-butylammonium hydrogen sulfate (22 g), and sodium hydroxide (21 g) in a mixture of dichloromethane (195 ml) and water (97.5 ml) was vigorously stirred at room temperature for 48 hours. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was added to n-hexane and pulverized to give N,N-dimethyl-4-(1,1-dimethyl-2-propynyloxy)benzenesulfonamide (6.4 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. additionThe residue was added to n-hexane

Sources & evidence

ORD record
ord-6e8e704a8b664dc186c1c06c50f4ad60
Source dataset
uspto-grants-1992_04
Patent number
US05104890

Reaction notes

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