Hydrochloric Acid → 3-Ethylisoxazole-5-carboxanilide

HRID 1590993Notes

Reaction equation

HRID 1590993 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([C:10]1[CH:14]=[C:13]([C:15](Cl)=[O:16])[O:12][N:11]=1)[CH3:9].O.Cl>ClCCl>[CH2:8]([C:10]1[CH:14]=[C:13]([C:15]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:16])[O:12][N:11]=1)[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6115AnilineHCID 129051013-Ethylisoxazole-5-carbonyl chloride

Product 1

HCID 156929113-Ethylisoxazole-5-carboxanilideYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11.7 g of aniline are added dropwise to 10.0 g of 3-ethylisoxazole-5-carbonyl chloride in 150 ml of dichloromethane, while cooling with ice. The mixture is stirred overnight at room temperature, water and concentrated hydrochloric acid are added and the organic phase is separated off, washed with sodium bicarbonate solution and evaporated down to give 11.8 g of 3-ethylisoxazole-5-carboxanilide as colorless crystals of melting point 122°-124° C.

Workup

  1. temperaturewhile cooling with ice
  2. customthe organic phase is separated off
  3. washwashed with sodium bicarbonate solution
  4. customevaporated down

Sources & evidence

ORD record
ord-ad954ba27e094bbe9e91c6b0a3497897
Source dataset
uspto-grants-1993_04
Patent number
US05205854

Reaction notes

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