Hydroxylamine → 3,4-Dichlorobenzylthioaceto-hydroxamic acid

HRID 261877Notes

Reaction equation

HRID 261877 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[CH2:5][CH2:6][C:7](O)=[S:8].OS(O)(=O)=O.ClC(Cl)C.[NH2:23][OH:24].C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[CH2:5][CH2:6][C:7]([NH:23][OH:24])=[S:8]

Participants

7

Reactant 5

HCID 787HydroxylamineHCID 1118Sulfuric AcidHCID 63651,1-DichloroethaneHCID 10942334Sodium MethoxideHCID 178526174HCID 178526174, compound

Product 1

HCID 867361013,4-Dichlorobenzylthioaceto-hydroxamic acidYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

20.2 g (0.08 mol) of 3,4-dichlorobenzylthioacetic acid are esterified with 10 ml of methanol, 0.6 ml of concentrated H2SO4 and 100 ml of dichloroethane. The mixture is heated under reflux for 4 hours, washed with water and with dilute bicarbonate solution, and dried. The mixture is evaporated in vacuo. The oily residue, in methanol, is treated with a solution of hydroxylamine (0.1 mol) in the presence of 0.18 mol of sodium methylate. After leaving the reactants in contact overnight, the mixture is evaporated to dryness in vacuo, the residue is taken up in water, the mixture is filtered over charcoal and the filtrate is precipitated with 3 N HCl, the product is extracted with ether, the extract is dried and evaporated and the product is crystallised in diisopropyl ether. 15 g of the stated product are obtained (yield 71%). Melting point: 75°-76° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 4 hours
  3. washwashed with water and with dilute bicarbonate solution
  4. customdried
  5. customThe mixture is evaporated in vacuo
  6. customAfter leaving the reactants in contact overnight
  7. customthe mixture is evaporated to dryness in vacuo
  8. filtrationthe mixture is filtered over charcoal
  9. customthe filtrate is precipitated with 3 N HCl
  10. extractionthe product is extracted with ether
  11. customthe extract is dried
  12. customevaporated
  13. customthe product is crystallised in diisopropyl ether

Sources & evidence

ORD record
ord-89f8b58841cf466d92e0ab3460a0ba0b
Source dataset
uspto-grants-1979_05
Patent number
US04152458

Reaction notes

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