Acetic Acid → HCID 4947826, compound

HRID 1885853Notes

Reaction equation

HRID 1885853 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 recrystallised from ether had m.p. 149°-150° C.

Sources & evidence

ORD record
ord-5b930418b5c74294b60b7a2c9ce8291f
Source dataset
uspto-grants-1992_09
Patent number
US05147875

Reaction notes

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