Diazomethane → HCID 10082838, compound

Participants

Reaction Steps

To a solution of 5-p-methoxybenzylthiotetrazole (7.00 g: 31.5 mMol.) in methanol (150 ml) is added under ice cooling a solution of diazomethane in ether (produced from 14 g of N-nitrosomethylurea), and the mixture is stirred for 1 hour and then concentrated. The residue is purified by Lobar column chromatography (toluene: ethyl acetate=5:1) to give 5-p-methoxybenzylthio-2-methyltetrazole [4.86 g: NMR δ(CDCl3) ppm: 3.78(s, 3H), 4.29(s, 3H), 4.38(s; 2H), 6.81-6.85, 7.30-7.34 (A2B2, 4H). IR ν(CHCl3) cm-1 : 1611, 1512, 1390, 1324, 1303. colorless oil. Yield: 65%] and 5-p-methoxybenzylthio-1-methyltetrazole [2.71 g: NMR δ(CDCl3) ppm: 3.79(s, 3H), 3.80(s, 3H), 4.49(s, 2H), 6.82-6.86, 7.27-7.31(A2B2, 4H). IR ν(CHCl3) cm-1 : 1613, 1513, 1465, 1305. colorless crystals. Yield: 36%].

Provenance & Evidence