4-Toluenesulfonyl chloride → HCID 20185710, compound

HRID 1706178Notes

Reaction equation

HRID 1706178 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][O:19][NH2:20])=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][O:19][NH:20][S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 120426O-((4-Methoxyphenyl)methyl)hydroxylamine

Product 1

HCID 20185710HCID 20185710, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of tosyl chloride (156.7 g) in pyridine (240 ml) was added dropwise to a solution of p-methoxybenzyloxyamine (102.3 g) in pyridine (210 ml) for 2.5 hours under cooling at 0°-5° C. and the mixture was stirred overnight at ambient temperature. The solvent was distilled off under reduced pressure and the residue was dissolved in ethyl acetate (1 l). The insoluble substances were filtered off, and the filtrate was washed three times with 2N hydrochloric acid, twice with water, dried over magnesium sulfate and evaporated to dryness under reduced pressure to give crystalline product, which was recrystallized from a mixture of ethylacetate and petroleum ether to give N-(p-methoxybenzyloxy)-p-toluenesulfonamide (162.2 g) in the form of crystals.

Workup

  1. temperatureunder cooling at 0°-5° C.
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate (1 l)
  4. filtrationThe insoluble substances were filtered off
  5. washthe filtrate was washed three times with 2N hydrochloric acid
  6. dry with materialtwice with water, dried over magnesium sulfate
  7. customevaporated to dryness under reduced pressure
  8. customto give crystalline product, which
  9. customwas recrystallized from a mixture of ethylacetate and petroleum ether

Sources & evidence

ORD record
ord-486e476f9c6744108c7ee2eb4446cc4a
Source dataset
uspto-grants-1980_06
Patent number
US04206156

Reaction notes

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