Hydrochloric Acid → HCID 131713567, compound

HRID 1461966Notes

Reaction equation

HRID 1461966 reaction equation
[Br:1]Br.[C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:19])=[C:9]([CH:18]=1)[NH:10][C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:4].C([O-])(=O)C.[Na+].Cl>O.C(O)(=O)C.CO.CS(C)=O>[Br:1][C:7]1[C:8]([OH:19])=[C:9]([CH:18]=[C:5]([C:3]#[N:4])[CH:6]=1)[NH:10][C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 517045Sodium AcetateHCID 13324573HCID 13324573, compound

Product 1

HCID 131713567HCID 131713567, compoundYield 74.8%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolvent2×HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1.1 g of bromine and 5 ml of acetic acid was added dropwise to a solution of 1.5 g of ethyl 5-cyano-2-hydroxyoxanilate and 1 g of sodium acetate in a mixed solution of 10 ml of dimethyl sulfoxide, 10 ml of methanol and 20 ml of acetic acid. After stirring the mixture for 30 minutes at room temperature, 6 ml of 2 normal hydrochloric acid and 200 ml of water were added to the reaction mixture and the product was extracted with a mixture of 30 ml of toluene and 40 ml of ethyl acetate. The extract was washed with water, dried, and then concentrated under reduced pressure. Crystals formed were washed with a mixture of ether and n-hexane to provide 1.5 g of ethyl 3-bromo-5-cyano-2-hydroxyoxanilate.

Workup

  1. extractionthe product was extracted with a mixture of 30 ml of toluene and 40 ml of ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customCrystals formed
  6. washwere washed with a mixture of ether and n-hexane

Sources & evidence

ORD record
ord-de2d0e6795624a8eb372fd1fdd3e7570
Source dataset
uspto-grants-1984_07
Patent number
US04457872

Reaction notes

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