Hydroxyamine hydrochloride → Acetamide, 2-((3,4-dichlorophenyl)amino)-N-hydroxy-

HRID 1707019Notes

Reaction equation

HRID 1707019 reaction equation
C[O-].[Na+].[Na].Cl.[NH2:6][OH:7].[Cl:8][C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][C:21]=1[Cl:22])[NH:12][CH2:13][C:14](OCC)=[O:15]>CO>[Cl:8][C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][C:21]=1[Cl:22])[NH:12][CH2:13][C:14]([NH:6][OH:7])=[O:15]

Participants

6

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 2727804Ethyl 2-(3,4-dichloroanilino)acetateHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 203276Acetamide, 2-((3,4-dichlorophenyl)amino)-N-hydroxy-Yield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of sodium methylate, that is to say 3.22 g (0.14 gram atom) of sodium in 75 ml of methanol is mixed in the cold with 4.9 g (0.07 mol) of hydroxylamine hydrochloride in solution in 100 ml of methanol, the sodium chloride is filtered off and 16.1 g (0.065 mol) of ethyl 3,4-dichloroanilinoacetate are added to the filtrate. The reactants are left in contact overnight, the mixture is evaporated to dryness in vacuo, the residue is taken up with water, the solution is filtered over charcoal and the product is precipitated with 3 N HCl and filtered off. Recrystallisation from ethyl acetate gives CRL 40,500. Melting point=138°-140° C. (with decomposition). Yield: 36%.

Workup

  1. filtrationthe sodium chloride is filtered off
  2. customthe mixture is evaporated to dryness in vacuo
  3. filtrationthe solution is filtered over charcoal
  4. customthe product is precipitated with 3 N HCl
  5. filtrationfiltered off
  6. customRecrystallisation from ethyl acetate
  7. customgives CRL 40,500

Sources & evidence

ORD record
ord-4891f60c608d44899ede60473289a204
Source dataset
uspto-grants-1980_06
Patent number
US04209523

Reaction notes

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