Hydrochloric Acid → 3-Ethylisoxazole-5-carboxanilide

HRID 1090015Notes

Reaction equation

HRID 1090015 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-803f5bed721f49bab3dbac2f5d8197d3
Source dataset
uspto-grants-1992_01
Patent number
US05080708

Reaction notes

Loading…