Hydrochloric Acid → 1-[3-(4-Chlorophenyl)-1,2-oxazol-5-yl]methanamine

HRID 1395465Notes

Reaction equation

HRID 1395465 reaction equation
[Br-].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([CH2:14][N+:15]34CN5CN(CN(C5)C3)C4)[O:11][N:10]=2)=[CH:5][CH:4]=1.Cl>CO>[NH2:15][CH2:14][C:12]1[O:11][N:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=2)[CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20339738HCID 20339738, compound

Product 1

HCID 27641631-[3-(4-Chlorophenyl)-1,2-oxazol-5-yl]methanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 205 g. portion of the product of Example 5 was dissolved in 1.5 l. of methanol and 250 ml. of concentrated hydrochloric acid was added. The mixture was stirred at reflux temperature overnight, and the solvent was then evaporated under vacuum. The residue was neutralized with aqueous sodium hydroxide and the product was extracted from the aqueous mixture with methylene dichloride and was purified by evaporating the solvent and recrystallizing the residue from ethanol-petroleum ether. The product was 78 g. of 5-aminomethyl-3-(4-chlorophenyl)isoxazole, m.p. 81°.

Workup

  1. temperatureat reflux temperature overnight
  2. customthe solvent was then evaporated under vacuum
  3. extractionthe product was extracted from the aqueous mixture with methylene dichloride
  4. customwas purified
  5. customby evaporating the solvent
  6. customrecrystallizing the residue from ethanol-petroleum ether

Sources & evidence

ORD record
ord-10fa5e704fcc4497afef9de6594f0517
Source dataset
uspto-grants-1980_05
Patent number
US04203994

Reaction notes

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