Pentyl nitrite → HCID 18793861, compound

Participants

Reaction Conditions

Reaction Steps

A solution of amyl nitrite (5.4 ml) in tetrahydrofuran (45 ml) was added dropwise to a stirred solution of ethyl 2-amino-4-thiazoleglyoxylate (4.00 g) (Aldrich) in tetrahydrofuran (25 ml) at 60° C. When the addition was complete (1 h) the mixture was stirred at 60° C. for a further 2 h. The solvent was evaporated and the residue partitioned between ethyl acetate and sodium bicarbonate solution. The organic phase was washed with water and brine, dried over magnesium sulphate and evaporated. The product (2.54 g) was isolated by column chromatography of the residue using gradient elution (Kieselgel: 2:1 to 1:1 hexane:ethyl acetate). νmax (CHCl3)/cm-1 1737 and 1696. δ (250 MHz, CDCl3), 1.42 (3H, t, J 7.11), 4.46 (2H, q, J 7.22), 8.84 (1H, J 1.95), 8.91 (1H, d, J 1.98).

Provenance & Evidence