Reaktion #3973

ord-6a823073ab7c4f51901f88aec89eb947

Reaktionsgleichung

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

Edukte

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

Reagenzien

CN(C)C=O
dimethylformamide

Lösungsmittel

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

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe product precipitated
  2. 2
    Filtrationis filtered off

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04722929uspto-grants-1988_02