Glycine → HCID 21835782, compound

HRID 1586552Notes

Reaction equation

HRID 1586552 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+].S(OCC)(O[CH2:29][CH3:30])(=O)=O.CN(C)[C:36](=O)[CH3:37]>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]([O:6][CH2:36][CH3:37])=[O:5])([O:16][CH2:29][CH3:30])=[O:15]

Participants

8

Reactant 6

HCID 750GlycineHCID 57872,4-Dichlorobenzoic AcidHCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 31374Dimethylacetamide3×

Product 1

HCID 21835782HCID 21835782, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 14452Copper carbonateCatalyst

Conditions

Temperature
80 °C

Procedure

47.8 g (0.25 mol) of 2,4-dichlorobenzoic acid, 22.5 g (0.3 mol) of glycine,1.5 g (6.8 mmol) of basic copper carbonate and 22 g (0.55 mol) of NaOH are introduced into 300 g of N,N-dimethylacetamide and heated to 80° C. 20.8 g (0.15 mol) of potassium carbonate are added, and the mixture is heated to 100° C. After 3.5 h at 100° C., the temperature is raised to 110° C., and the mixture is stirred at 110° C. for 3.5 h, during which 100 g of N,N-dimethylacetamide are added. After a further 100 g of N,N-dimethylacetamide has been added the mixture is heated at 120° C. for 2.5 h and at 140-150° C. for 2.5 h. After cooling to 80° C., 139.8 g (0.9 mol) of diethyl sulfate are added dropwise over the course of 2 h and, after stirring at 80° C. for 45 min, excess diethyl sulfate is destroyed by adding ammonia. 350 g of water are added to the reaction mixture, and the product is extracted with xylene. 352 g of xylene extract with a product content of about 0.17 g/g are obtained, corresponding to 59.8 g (84%) of ethyl N-carbethoxymethylene-4-chloroanthranilate.

Workup

  1. temperaturethe mixture is heated to 100° C
  2. temperaturethe temperature is raised to 110° C.
  3. additionare added
  4. temperatureis heated at 120° C. for 2.5 h and at 140-150° C. for 2.5 h
  5. temperatureAfter cooling to 80° C.
  6. customexcess diethyl sulfate is destroyed
  7. additionby adding ammonia
  8. addition350 g of water are added to the reaction mixture
  9. extractionthe product is extracted with xylene
  10. extraction352 g of xylene extract with a product content of about 0.17 g/g

Sources & evidence

ORD record
ord-13fe10d5ca354a0a828fc05f209c8cdf
Source dataset
uspto-grants-1999_08
Patent number
US05945556

Reaction notes

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