Hydrochloric Acid → 3,5-dichloro-2-amino-N-(2-hydroxyethoxy)benzamide

HRID 449795

Reaction equation

HRID 449795 reaction equation
[Cl:1][C:2]1[C:3]([NH2:13])=[C:4]([CH:9]=[C:10]([Cl:12])[CH:11]=1)[C:5]([O:7]C)=O.[NH2:14][O:15][CH2:16][CH2:17][OH:18].C[O-].[Na+].Cl>CO.O>[Cl:1][C:2]1[C:3]([NH2:13])=[C:4]([CH:9]=[C:10]([Cl:12])[CH:11]=1)[C:5]([NH:14][O:15][CH2:16][CH2:17][OH:18])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 613050Methyl 2-amino-3,5-dichlorobenzoateHCID 3014186Ethanol, 2-(aminooxy)-HCID 10942334Sodium Methoxide

Product 1

HCID 866307723,5-dichloro-2-amino-N-(2-hydroxyethoxy)benzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

9 g (40.9 mmol) of methyl 3,5-dichloro-2-aminobenzoate and 6.3 g (81.8 mmol) of 2-(aminooxy)ethanol are initially charged in 90 ml of methanol, and 22.1 g (122.7 mmol) of sodium methoxide as a 30% strength solution in methanol are added dropwise at 20° C. The mixture is stirred at 50° C. overnight. The mixture is cooled and poured onto 400 ml of water, and the pH is adjusted to 3 using 1 N hydrochloric acid. The mixture is extracted 3 times with in each case 150 ml of ethyl acetate and the extracts are dried with sodium sulphate and concentrated using a rotary evaporator.

Workup

  1. temperatureThe mixture is cooled
  2. extractionThe mixture is extracted 3 times with in each case 150 ml of ethyl acetate
  3. dry with materialthe extracts are dried with sodium sulphate
  4. concentrationconcentrated
  5. customa rotary evaporator

Sources & evidence

ORD record
ord-97aeb5b5832340eea79b357341d5235c
Source dataset
uspto-grants-2013_07
Patent number
US08486934B2

Linked notes

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