Acetic Acid → HCID 4947826, compound

HRID 412026Notes

Reaction equation

HRID 412026 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11]([O-:14])(=O)[CH3:12].[Na+].[C:16]([OH:19])(=O)[CH3:17]>CC(C)=O>[CH2:3]([O:14][C:11]1[CH:12]=[CH:8][CH:2]=[CH:1][C:17]=1[C:16]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([NH2:10])=[O:9])=[O:19])[CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6942AnthranilamideHCID 517045Sodium Acetate

Product 1

HCID 4947826HCID 4947826, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-propoxybenzoic acid (5 g) in thionyl chloride (20 ml) was heated under reflux for three hours. Thionyl chloride was removed under reduced pressure and the residue was azeotroped with toluene to yield the acid chloride as a yellow oil (5.5 g). A solution of anthranilamide (3.77 g) in a mixture of saturated aqueous sodium acetate (20 ml) and acetic acid (20 ml) was added to the yellow oil in acetone (4 ml). The resulting solution was stirred at ambient temperature for one hour to yield as a light brown precipitate 2-(2-propoxybenzamido)benzamide, 3.78 g. A sample recrystallized from ether had m.p. 149-150° C.

Sources & evidence

ORD record
ord-0a2e4590f9da4e6c823e193eb06d477b
Source dataset
uspto-grants-2003_05
Patent number
US06562830B1

Reaction notes

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