Réaction #2298613

ord-cf0ed24154e14f5f9a947583dc6bd10b

Équation de réaction

CC(=O)OC(C)=O
acetic anhydride
COC(=O)c1sc(C)c(C)c1N
methyl 3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
COC(=O)c1scc(C)c1NC=O
3-(formylamino)-4-methyl-2-thiophenecarboxylic acid methyl ester
Rendement 95.0%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurewhile cooling in an ice bath
  2. 2
    AutreThe cooling bath was removed
  3. 3
    workup.ADDITIONThe reaction mixture was diluted with water (100 mL)
  4. 4
    Filtrationthe solid product collected by vacuum filtration

Mode opératoire

Formic acid (53 mL) was added to acetic anhydride (53 mL) while cooling in an ice bath. Solid methyl 3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester (1, 18.2 g, 0.11 mol) was added to the cold solution in small portions. The cooling bath was removed and the resulting suspension was stirred at room temperature for 4 hours. The reaction mixture was diluted with water (100 mL) and the solid product collected by vacuum filtration to yield 3-(formylamino)-4-methyl-2-thiophenecarboxylic acid methyl ester (20.2 g, 95% yield) as a white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: USRE039267E1uspto-grants-2006_09