2,6-Dichlorobenzoyl chloride → Benzamide, 2,6-dichloro-N-[5-(4-chlorophenyl)-3-isoxazolyl]-

HRID 2059223Notes

Reaction equation

HRID 2059223 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([NH2:13])[CH:9]=2)=[CH:4][CH:3]=1.[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:16]=1[C:17](Cl)=[O:18]>C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:16]=1[C:17]([NH:13][C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[O:12][N:11]=1)=[O:18]

Participants

4

Reactant 2

HCID 783922,6-Dichlorobenzoyl chlorideHCID 13035539JR-9574, 5-(4-Chlorophenyl)isoxazol-3-amine, 97%

Product 1

HCID 157868Benzamide, 2,6-dichloro-N-[5-(4-chlorophenyl)-3-isoxazolyl]-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-(4-Chlorophenyl)-3-aminoisoxazole (25 grams) was placed in a 500 ml. 3-necked flask under an atmosphere of nitrogen. Following the addition of 150 ml. of toluene, the reaction mixture was stirred continuously and treated in rapid fashion (15 minutes), with 2,6-dichlorobenzoylchloride (60 grams). The mixture was then heated to reflux for 18 hours and allowed to gradually cool to room temperature. When the reaction mixture was further cooled to approximately 0° C. the final product precipitated. The product was filtered and recrystallized from acetone to yield 28 grams, m.p. 228°-229° C.

Workup

  1. additionthe addition of 150 ml
  2. temperatureThe mixture was then heated
  3. temperatureto reflux for 18 hours

Sources & evidence

ORD record
ord-9ca5d85a548b4379b3a9a6ae146f8948
Source dataset
uspto-grants-1982_03
Patent number
US04322429

Reaction notes

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