Ethanol → HCID 21835786, compound

HRID 1741345Notes

Reaction equation

HRID 1741345 reaction equation
[C:1]([CH:4]=[N:5][C:6]1[C:7](=[CH:11][CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:8]([OH:10])=[O:9])([OH:3])=[O:2].S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[C:1]([CH:4]=[N:5][C:6]1[C:7](=[CH:11][CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:8]([OH:10])=[O:9])([O:3][CH2:21][CH3:22])=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric Acid2×HCID 19597249HCID 19597249, compound

Product 1

HCID 21835786HCID 21835786, compoundYield 73%

Procedure

74.5 g (324.8 mmol) of N-carboxymethylene-4-chloroanthranilic acid are suspended in 1660 g of ethanol, 2.9 g (2.96 mmol) of concentrated sulfuric acid are added and the mixture is heated at the boiling point for 10 hours. After a reaction time of 5 hours, the same amount of sulfuric acid is again added. After 10 hours, the ethanol is distilled off and the product which precipitates out is filtered off in the cold and washed with cold ethanol. 55.5 g (0.22 mol, 73%) of N-carboethoxymethylene-4-chloro-anthranilic acid are obtained.

Workup

  1. temperaturethe mixture is heated at the boiling point for 10 hours
  2. distillationthe ethanol is distilled off
  3. customthe product which precipitates out
  4. filtrationis filtered off in the cold
  5. washwashed with cold ethanol

Sources & evidence

ORD record
ord-bcafaaa5244e43208bf4d3b96253f486
Source dataset
uspto-grants-1999_10
Patent number
US05973189

Reaction notes

Loading…