Triethylamine hydrochloride → HCID 178442550, compound

Reaction equation

[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH3:26])[C:24]#[N:25])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:27]=[N+:28]=[N-:29].[Na+].Cl.C(N(CC)CC)C>CN(C)C=O>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([C:24]3[NH:29][N:28]=[N:27][N:25]=3)[CH3:26])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Procedure

3 g of (RS)-7(4,5-diphenyl-2-oxazolyl)-2-methylheptanenitrile in 30 cm3 of dimethylformamide are treated with twice 1.7 g of sodium azide and twice 3.6 g of triethylamine hydrochloride under the (time and temperature) conditions defined in Example 1. After treatment, the product of the reaction is chromatographed on a column 2 cm in diameter containing 78 g of silica gel (50 to 200μ). The column is eluted, collecting 200 cm3 fractions, with 1 liter of diisopropyl ether and then with 1.6 liters of a diisopropyl ether/ethyl acetate (95:5 by volume) mixture. The fractions from the last eluent mixture are concentrated to dryness under reduced pressure (0.2 kPa). 2.3 g (68%) of (RS)-5-[7-(4,5-diphenyl-2-oxazolyl)-2-heptyl]-1H-tetrazole are obtained in the form of a yellowish oil.