Trityl chloride → 5-(4'-Methyl[1,1'-biphenyl]-2-yl)-1-(triphenylmethyl)-1H-tetrazole

Participants

Reaction Steps

4'-Methylbiphenyl-2-nitrile (preparation described in European patent application 0253310, published on 20.01.88) (10.00 g, 51.7 mmol, 1 eq), tri-n-butyltin chloride (14.0 mL, 51.7 mmol, 1 eq), sodium azide (3.4 g, 51.7 mmol, 1 eq), and xylene (50 mL) were mixed and refluxed for 64 h after which the reaction mixture was cooled to room temperature. 10.0N NaOH (6.10 mL, 0.061 mmol, 1.2 eq) and trityl chloride (14.99 g, 53.8 mmol, 1.04 eq) were then added and the mixture stirred for 24 h after which water (39 mL) and heptane (100 mL) were added. The resultant slurry was stirred at 0° C. for 1.5 h. The resultant solids thus obtained were filtered, washed with water (2×55 mL) washed once with 3:2 heptane/toluene (55 mL) and dried overnight under high vacuum to yield 19.97 g of a light yellow powder: mp 148.0°-155.0° C. (dec.). These solids were slurried in ethyl acetate (75 mL) and filtered to yield 15.0 g of a light yellow powder: mp 164.0°-165.5° C. (dec.). NMR (CDCl3) δ 7.91 (d,1H,J=9Hz); 7.53-7.18 (m,13H); 7.02-6.84 (m,9H); 2.25 (s,3H). ##STR76##

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