Reacción #3973

ord-6a823073ab7c4f51901f88aec89eb947

Ecuación de reacción

CC(=O)O
acetic acid
COc1cc(C(=O)O)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1
8-(2-methoxy-4-carboxy-phenyl)-1H,-3H-purin-2,6-dione
N
ammonia
O
water
→
COc1cc(C(N)=O)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1
8-(2-Methoxy-4-aminocarbonyl-phenyl)-1H,3H-purin-2,6-dione

Reactantes

CC(=O)O
acetic acid
COc1cc(C(=O)O)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1
8-(2-methoxy-4-carboxy-phenyl)-1H,-3H-purin-2,6-dione
N
ammonia
O
water

Reactivos

CN(C)C=O
dimethylformamide

Disolventes

CN(C)C=O
dimethylformamide
O=S(Cl)Cl
thionyl chloride
O=S(Cl)Cl
thionyl chloride
CN(C)C=O
dimethylformamide

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothe product precipitated
  2. 2
    Filtraciónis filtered off

Procedimiento

A quantity of 2.3 gm of 8-(2-methoxy-4-carboxy-phenyl)-1H,-3H-purin-2,6-dione are refluxed for one hour in 50 ml of thionyl chloride with the addition of 1 drop of dimethylformamide. The excess thionyl chloride is drawn off, and the residue is stirred for 16 hours at ambient temperature with a solution of ammonia in dimethylformamide. The dimethylformamide is drawn off, the remainder is mixed with water and acidified with glacial acetic acid, and the product precipitated is filtered off.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04722929uspto-grants-1988_02