Glycine → HCID 19597249, compound

HRID 1586550Notes

Reaction equation

HRID 1586550 reaction equation
[OH-].[Na+].Cl[C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].[NH2:14][CH2:15][C:16]([OH:18])=[O:17].C(=O)([O-])[O-].[K+].[K+]>O.C(=O)([O-])[O-].[Cu+2]>[C:16]([CH:15]=[N:14][C:4]1[C:5](=[CH:9][CH:10]=[C:11]([Cl:13])[CH:12]=1)[C:6]([OH:8])=[O:7])([OH:18])=[O:17]

Participants

7

Reactant 4

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

Product 1

HCID 19597249HCID 19597249, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 14452Copper carbonateCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

20 g (0.5 mol) of NaOH are dissolved in 100 ml of water, and 38.2 g (0.2 mol) of 2,4-dichlorobenzoic acid, 22.5 g (0.3 mol) of glycine and 1.4 g (6 mmol) of basic copper carbonate are added. The mixture is heated to 80° C., and 28 g (0.2 mol) of potassium carbonate are added. It is heated at 100° C. for 3 h. The filtrate after filtration with suction while hot is added to 100 ml of water and adjusted to pH 1-2 with hydrochloric acid. The product then precipitates and is filtered with suction and dried. 41 g (0.18 mol; 89%) of N-carboxymethylene-4-chloroanthranilic acid are obtained.

Workup

  1. temperatureIt is heated at 100° C. for 3 h
  2. filtrationThe filtrate after filtration with suction
  3. additionwhile hot is added to 100 ml of water
  4. customThe product then precipitates
  5. filtrationis filtered with suction
  6. customdried

Sources & evidence

ORD record
ord-5b048905c5294dde8c467d7b1b7a02a3
Source dataset
uspto-grants-1999_08
Patent number
US05945556

Reaction notes

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