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

HRID 1834738Notes

Reaction equation

HRID 1834738 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 1 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 1 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-5fa5b5ce5e27428fadb3945f27866816
Source dataset
uspto-grants-1978_01
Patent number
US04071350

Reaction notes

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