Réaction #60036

ord-1d584f7ca362454b88ea8b457a67bd66

Équation de réaction

N#Cc1ccc(C(=O)Cc2ncc[nH]2)cc1
4-(2-imidazolylacetyl)benzenecarbonitrile
COC(OC)N(C)C
N,N-dimethylformamide dimethyl acetal
→
CN(C)/C=C(/C(=O)c1ccc(C#N)cc1)c1ncc[nH]1
4-[(2E)-3-(dimethylamino)-2-imidazolylprop-2-enoyl]benzenecarbonitrile

Réactifs

N#Cc1ccc(C(=O)Cc2ncc[nH]2)cc1
4-(2-imidazolylacetyl)benzenecarbonitrile
COC(OC)N(C)C
N,N-dimethylformamide dimethyl acetal

Réactifs

Aucun

Conditions de réaction

Température
75°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe DMFDMA was then removed under reduced pressure
  2. 2
    Autredried under high vacuum for several hours

Mode opératoire

A mixture of 4-(2-imidazolylacetyl)benzenecarbonitrile (0.30 M) and N,N-dimethylformamide dimethyl acetal (DMFDMA) (80 ml) was stirred for 12 h at 75° C. The DMFDMA was then removed under reduced pressure and dried under high vacuum for several hours giving an orange-yellow solid 4-[(2E)-3-(dimethylamino)-2-imidazolylprop-2-enoyl]benzenecarbonitrile in quantitative yield. The enaminone product was typically used without further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07425557B2uspto-grants-2008_09