O-Methylhydroxylamine → N-methoxy-2,4,5-trichlorobenzenesulfonamide

HRID 838797Notes

Reaction equation

HRID 838797 reaction equation
[CH3:1][O:2][NH2:3].[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:6]=1[S:13](Cl)(=[O:15])=[O:14].[OH-].[Na+]>CCOCC.O.O1CCCC1>[CH3:1][O:2][NH:3][S:13]([C:6]1[CH:7]=[C:8]([Cl:12])[C:9]([Cl:11])=[CH:10][C:5]=1[Cl:4])(=[O:15])=[O:14]

Participants

7

Reactant 3

HCID 4113O-MethylhydroxylamineHCID 14798Sodium HydroxideHCID 275752,4,5-Trichlorobenzenesulfonyl chloride

Product 1

HCID 20324727N-methoxy-2,4,5-trichlorobenzenesulfonamide

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

5.0 g. of methoxy amine was dissolved in 100 ml. of H2O. Then, 14.0 g. of 2,4,5-trichlorobenzene sulfonyl chloride dissolved in 25 ml. of tetrahydrofuran was added under high speed mechanical stirring. Then 8.8 g. of sodium hydroxide in a 50% solution + 10 ml. of water was dropped in at room temperature. An exothermic reaction took place and the temperature went up to 37.5° C. When the reaction subsided, it was stirred at room temperature for two hours and the solid was then filtered off and stirred into 150 ml. of ether for one hour. The solid was removed by filtration to yield 11.3 g. of product. The product was redissolved in ether. The ether was evaporated to yield 7.4 g. of product, m.p. 163°-166° C.

Workup

  1. customAn exothermic reaction
  2. customwent up to 37.5° C
  3. filtrationthe solid was then filtered off
  4. stirringstirred into 150 ml
  5. waitof ether for one hour
  6. customThe solid was removed by filtration
  7. customto yield 11.3 g
  8. customThe ether was evaporated
  9. customto yield 7.4 g

Sources & evidence

ORD record
ord-68f8e37260514a05a5f0a87f0671f550
Source dataset
uspto-grants-1978_06
Patent number
US04093445

Reaction notes

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