Sodium Hydroxide → N-(3-Benzyloxypropoxymethyl)-2,4,6-trichloro-N-methylbenzenesulfonamide

HRID 424624Notes

Reaction equation

HRID 424624 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[C:17]=1[S:24]([N:27]([CH2:29]Cl)[CH3:28])(=[O:26])=[O:25]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][CH2:28][N:27]([CH3:29])[S:24]([C:17]1[C:16]([Cl:15])=[CH:21][C:20]([Cl:22])=[CH:19][C:18]=1[Cl:23])(=[O:25])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 3479713-Benzyloxy-1-propanolHCID 66703409HCID 66703409, compound

Product 1

HCID 66703421N-(3-Benzyloxypropoxymethyl)-2,4,6-trichloro-N-methylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

A soln. of 3-benzyloxy-1-propanol (4.08 g, 3.90 ml, 24.5 mmol) and tetra-n-butylammonium hydrogen sulfate (1.78 g, 5.25 mmol) in toluene (100 ml) was cooled in an ice-bath and 35% strength sodium hydroxide solution (49.0 g, 140 ml, 1.22 mol) was added. A soln. of 2,4,6-trichloro-N-chloromethyl-N-methylbenzenesulfonamide (7.10 g, 22 mmol) in MC (60 ml) was then slowly added dropwise. The mixture was then stirred at RT for 15-20 h. Thereafter, the phases were separated and the organic phase was washed neutral with water (6×50 ml) and saturated sodium chloride solution (2×40 ml), dried with Na2SO4 and concentrated i. vac. The crude product was purified by means of flash chromatography with cyclohexane/EtOAc (9:1).

Workup

  1. customThereafter, the phases were separated
  2. washthe organic phase was washed neutral with water (6×50 ml) and saturated sodium chloride solution (2×40 ml)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated i
  5. customThe crude product was purified by means of flash chromatography with cyclohexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-7e61bd1a275f4bc6937c4110fbe709d6
Source dataset
uspto-grants-2012_01
Patent number
US08106055B2

Reaction notes

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