Triethylamine → HCID 430947, compound

HRID 1604990Notes

Reaction equation

HRID 1604990 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][C:11](Cl)=[N:12][OH:13])=[N:2]1.C([N:17](CC)CC)C>C(Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][C:11](=[N:12][OH:13])[NH2:17])=[N:2]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 85444374HCID 85444374, compound

Product 1

HCID 430947HCID 430947, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 1,2-benzisoxazole-3-acetohydroximic chloride (0.4 g) in chloroform (80 ml) was added a solution of triethylamine (3.2 g) in chloroform (40 ml) under ice-cooling and the mixture was stirred for 4 hours under ice-cooling. The mixture was distilled under a reduced pressure to remove the solvent. To the residue was added benzene and the precipitate of triethylamine hydrochloride was filtered off. To the filtrate was passed through ammonia gas under ice-cooling for a period of 1 hour and further at reflux temperature for 3 hours. The mixture was distilled under a reduced pressure to remove the solvent and the residue was subjected to silica gel column chromatography and eluted with 5 % methanol-chloroform. The resulting crystallines were recrystallized from ethanol to give the desired compound (0.1 g). m.p. 160° to 162°C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. distillationThe mixture was distilled under a reduced pressure
  4. customto remove the solvent
  5. additionTo the residue was added benzene
  6. filtrationthe precipitate of triethylamine hydrochloride was filtered off
  7. temperaturecooling for a period of 1 hour
  8. temperaturefurther at reflux temperature for 3 hours
  9. distillationThe mixture was distilled under a reduced pressure
  10. customto remove the solvent
  11. washeluted with 5 % methanol-chloroform
  12. customThe resulting crystallines were recrystallized from ethanol

Sources & evidence

ORD record
ord-41c425d1aeb94c4aa750e941d86ed9f5
Source dataset
uspto-grants-1976_04
Patent number
US03948928

Reaction notes

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