Hydrochloric Acid → HCID 19597249, compound

HRID 1586549Notes

Reaction equation

HRID 1586549 reaction equation
Cl[C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:12][CH2:13][C:14]([OH:16])=[O:15].[OH-].[Na+].C([O-])([O-])=O.[K+].[K+].Cl>CC(N(C)C)=O.O.C(=O)([O-])[O-].[Cu+2]>[C:14]([CH:13]=[N:12][C:2]1[C:3](=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:4]([OH:6])=[O:5])([OH:16])=[O:15]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 750GlycineHCID 57872,4-Dichlorobenzoic AcidHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 19597249HCID 19597249, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 14452Copper carbonateCatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

47.8 g(0.25 mol) of 2,4-dichlorobenzoic acid are dissolved in 500 g of dimethylacetamide, 26.3 g (0.35 mol) of glycine and 1.7 g (7.5 mmol) of basic copper carbonate are added and the mixture is heated to 80° C. After addition of 24 g (0.6 mol) of NaOH and 22.5 g (0.16 mol) of K2CO3, the mixture is heated at 140° C. for 5 h. It is cooled to room temperature, diluted with 200 ml of water and adjusted to pH 2 with hydrochloric acid, and the crystalline product is filtered off. 43.9 g (0.19 mol, 77%) of N-carboxymethylene-4-chloroanthranilic acid are obtained.

Workup

  1. temperaturethe mixture is heated at 140° C. for 5 h
  2. temperatureIt is cooled to room temperature
  3. filtrationthe crystalline product is filtered off

Sources & evidence

ORD record
ord-42768a5f864f48cab6b268986e0f2dae
Source dataset
uspto-grants-1999_08
Patent number
US05945556

Reaction notes

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