Hydrochloric Acid → N-(3-bromo-2-methylphenyl)-2-(hydroxyimino)acetamide

HRID 513235Notes

Reaction equation

HRID 513235 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[NH2:10][OH:11].OS(O)(=O)=O.Cl.Cl[C:19](Cl)(Cl)[CH:20]([OH:22])O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:8][C:20](=[O:22])[CH:19]=[N:10][OH:11])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 24436Sodium SulfateHCID 1235383-Bromo-o-toluidineHCID 159255Hydroxylamine, sulfate (1:1)

Product 1

HCID 72595240N-(3-bromo-2-methylphenyl)-2-(hydroxyimino)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

A mixture of 3-Bromo-2-methyl-phenylamine (15.6 g, 0.084 mol), NH2OH H2SO4 (71.25 g, 0.5 mol), conc. HCl (8.8 mL) in H2O (90 mL) is slowly added to a solution of chloral hydrate (15.2 g, 0.09 mol), Na2SO4 (71.25 g, 0.44 mol) in H2O (255 mL) then stirred at 35° C. for 1 h, 52° C. for 1.5 h, 75° C. for 1 h. After the reaction, the mixture is filtered and the solid is dried under vacuum to give product.

Workup

  1. customAfter the reaction
  2. filtrationthe mixture is filtered
  3. customthe solid is dried under vacuum
  4. customto give product

Sources & evidence

ORD record
ord-e948ff0011294baaa4103f6f9d16b35b
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

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