Reaction #349285

ord-2aba2e29f55c4639b0f13c47850e352e

Reaction equation

CC(=O)Oc1ccccc1C(=O)O
aspirin
NC(=O)c1ccccc1O
salicylamide
CC(=O)Oc1c(C(=O)[O-])cccc1-c1ccccc1C(N)=O
2-(carbamoyl)phenyl-2-acetoxybenzoate
CC(=O)Oc1c(C(=O)[O-])cccc1-c1ccccc1C(N)=O
2-(carbamoyl)phenyl-2-acetoxybenzoate
→
O=C(O)c1ccccc1O
salicylic acid
NC(=O)c1ccccc1O
salicylamide

Reactants

—
( B )
CC(=O)Oc1ccccc1C(=O)O
aspirin
NC(=O)c1ccccc1O
salicylamide
CC(=O)Oc1c(C(=O)[O-])cccc1-c1ccccc1C(N)=O
2-(carbamoyl)phenyl-2-acetoxybenzoate
—
( A )
CC(=O)Oc1c(C(=O)[O-])cccc1-c1ccccc1C(N)=O
2-(carbamoyl)phenyl-2-acetoxybenzoate

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

The following experiments illustrate (A) the reduced gastric toxicity of 2-(carbamoyl)phenyl-2-acetoxybenzoate relative to a physical mixture of aspirin and salicylamide and (B) the in vivo hydrolysis of 2-(carbamoyl)phenyl-2-acetoxybenzoate to give plasma concentrations of salicylic acid and salicylamide.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04153691uspto-grants-1979_05