Carbon Tetrachloride → HCID 15613883, compound

HRID 2291710Notes

Reaction equation

HRID 2291710 reaction equation
C([O-])(=O)C.[Na+].[F:6][C:7]([F:15])([F:14])[C:8]1[CH:12]=[C:11]([NH2:13])[O:10][N:9]=1.ClCl.C(Cl)(Cl)(Cl)[Cl:19].[OH-].[Na+]>C(O)(=O)C>[F:6][C:7]([F:15])([F:14])[C:8]1[C:12]([Cl:19])=[C:11]([NH2:13])[O:10][N:9]=1

Participants

7

Reactant 5

HCID 5943Carbon TetrachlorideHCID 14798Sodium HydroxideHCID 24526ChlorineHCID 517045Sodium AcetateHCID 139139963-(Trifluoromethyl)-1,2-oxazol-5-amine

Product 1

HCID 15613883HCID 15613883, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic acid (7 ml) and anhydrous sodium acetate (0.57 g, 7.00 mmole) were added to 3-trifluoromethyl-5-aminoisoxazole (1.06 g, 7.00 mmole) with stirring at room temperature and a solution of chlorine in carbon tetrachloride (8.5 ml, 1 mole/1, 8.40 mmole) was then added dropwise to the mixture. After stirring for 1 hour at room temperature, the reaction mixture was poured into ice-water (70 ml) and it was adjusted to pH 10 with a solution of sodium hydroxide. It was extracted with methylene chloride. After the extract was dried with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to give a brown viscous liquid (0.80 g). This product was purified by column chromatography on silica gel to give a dark red liquid (0.54 g). It was further distilled under reduced pressure to give the title compound as a colorless liquid. Yield: 0.41 g (31.5%), b.p. 73.0°-74.5° C./4.0 mmHg. The structure of this product was confirmed with IR and NMR.

Workup

  1. stirringAfter stirring for 1 hour at room temperature
  2. extractionIt was extracted with methylene chloride
  3. dry with materialAfter the extract was dried with anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-62dbae24b16a40eb82c555ef65fe3e16
Source dataset
uspto-grants-1989_01
Patent number
US04797492

Reaction notes

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