Réaction #343017

ord-9125cb95be464dd5b618a84b0d95ab93

Équation de réaction

CC(=O)OCCc1ccccc1S(=O)(=O)N=C=O
sulfonyl isocyanate
CC(=O)OCCc1ccccc1S(=O)(=O)N=C=O
2-[2-(acetyloxy)ethyl]benzenesulfonyl isocyanate
COc1cc(OC)nc(N)n1
2-amino-4,6-dimethoxypyrimidine
→
COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2ccccc2CCOC(C)=O)n1
2-[2-(acetyloxy)ethyl]-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide
Rendement 54.8%

Réactifs

CC(=O)OCCc1ccccc1S(=O)(=O)N=C=O
sulfonyl isocyanate
CC(=O)OCCc1ccccc1S(=O)(=O)N=C=O
2-[2-(acetyloxy)ethyl]benzenesulfonyl isocyanate
COc1cc(OC)nc(N)n1
2-amino-4,6-dimethoxypyrimidine

Réactifs

Aucun

Solvants

CC#N
acetonitrile

Conditions de réaction

Température
50°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    FiltrationFiltration of the insoluble solids
  2. 2
    Lavagewashing with 1-chlorobutane
  3. 3
    Autreby drying

Mode opératoire

To a stirred solution of 2.3 g of the sulfonyl isocyanate from Example 7 in 25 ml dry acetonitrile was added 1.2 g of 2-amino-4,6-dimethoxypyrimidine. The reaction mixture was warmed to 50° C. for 11/4 hour and then stirred at room temperature for 2 days. Filtration of the insoluble solids and washing with 1-chlorobutane followed by drying afforded 1.8 g of 2-[2-(acetyloxy)ethyl]-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide as a light yellow solid, m.p. 160°-162° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04699650uspto-grants-1987_10