3,5-Dibromosalicylic acid → N-[4-[1-(4-chlorophenyl)ethenyl]phenyl]-2-hydroxy-3,5-dibromobenzamide

HRID 280034

Reaction equation

HRID 280034 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[C:4]([C:5]([OH:7])=O)[C:3]=1[OH:12].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH2:21])=[CH:16][CH:15]=1.P(Cl)(Cl)Cl>>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([C:20]([C:17]2[CH:16]=[CH:15][C:14]([NH:13][C:5](=[O:7])[C:4]3[CH:8]=[C:9]([Br:11])[CH:10]=[C:2]([Br:1])[C:3]=3[OH:12])=[CH:19][CH:18]=2)=[CH2:21])=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 184643,5-Dibromosalicylic acidHCID 24387Phosphorus trichlorideHCID 136083361-(4-Aminophenyl)-1-(4-chlorophenyl)ethylene

Product 1

HCID 13608338N-[4-[1-(4-chlorophenyl)ethenyl]phenyl]-2-hydroxy-3,5-dibromobenzamide

Procedure

Using the reaction conditions of Example 2, 5.92 g (0.02 mole) of 3,5-dibromosalicylic acid and 5.32 g (0.02 mole) of 1-(4-aminophenyl)-1-(4-chlorophenyl)ethylene in the presence of phosphorus trichloride were reacted to give 4.26 of purified N-[4-[1-(4-chlorophenyl)ethenyl]phenyl]-2-hydroxy-3,5-dibromobenzamide, m.p. 181°-183°.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-decb5f5514e0443994821db67f0a99e6
Source dataset
uspto-grants-1986_05
Patent number
US04587361

Linked notes

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