Chlorosuccinimide → HCID 178525280, compound

HRID 1390040Notes

Reaction equation

HRID 1390040 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[O:4][N:3]=1.[Cl:11]N1C(=O)CCC1=O>CN(C)C=O>[Cl:11][C:6]1[C:2]([OH:1])=[N:3][O:4][C:5]=1[CH2:7][C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178525217HCID 178525217, compound

Product 1

HCID 178525280HCID 178525280, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.3 g (30 mmoles) of 3-hydroxyisoxazol-5-ylacetic acid in 10 ml of N,N-dimethylformamide were added 4.81 g (36 mmole) of N-chlorosuccinimide, with ice-cooling and stirring. The mixture was left to stand at room temperature for 15 hours, after which the N,N-dimethylformamide was distilled off under reduced pressure and ethyl acetate was added. The mixture was then extracted with an aqueous solution of sodium hydrogen carbonate and then the pH of the extract was adjusted to a value below 1.0 by addition of concentrated hydrochloric acid. After drying the solution, the solvent was distilled off and the residue was recrystallized from a 1:5 by volume mixture of ethyl acetate and cyclohexane, to give 3.2 g (60%) of the title compound, melting point 155° C.

Workup

  1. temperaturewith ice-cooling
  2. waitThe mixture was left
  3. distillationafter which the N,N-dimethylformamide was distilled off under reduced pressure and ethyl acetate
  4. additionwas added
  5. extractionThe mixture was then extracted with an aqueous solution of sodium hydrogen carbonate
  6. additionthe pH of the extract was adjusted to a value below 1.0 by addition of concentrated hydrochloric acid
  7. customAfter drying the solution
  8. distillationthe solvent was distilled off
  9. customthe residue was recrystallized from a 1:5 by volume mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-5713f8905d284f29ae3f51f6dc65ac37
Source dataset
uspto-grants-1981_01
Patent number
US04247548

Reaction notes

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