Triethylamine → HCID 11820223, compound

Participants

Reaction Steps

4-Nitrobenzylbromide (25.4 g, 0.12 mol) was added to a solution of 1H-1,2,3-triazole (8.12 g, 0.12 mol) and triethylamine (11.88 g, 0.12 mol) in anhydrous acetonitrile. The mixture was refluxed for 1 h, cooled to room temperature and the precipitated NEt3. HBr filtered off. The solvent was removed under vacuum and the residue chromatographed through silica gel eluting with CH2Cl2 (100) to CH2Cl2 /MeOH (95.5) to give 2-products. The more polar product was identified as the title-1-isomer (13 g, 54%); mp 114°-116° C. δ (250 MHz, CDCl3) 5.72 (2H, s, CH2), 7.38 (2H, d, J=9 Hz, Ar-H), 7.64 (1H, s, Ar-H), 7.78 (1H, s, Ar-H), 8.18 (2H, d, J=9 Hz, Ar-H). The less polar, minor isomer was identified as the 2-alkylation product (2.25 g, 9%), mp 112°-113° C. δ (250 MHz, CDCl3) 5.72 (2H, s, CH2), 7.40 (2H, d, J=9 Hz, Ar-H), 7.66 (2H, s, Ar-H), 8.18 (2H, d, J=9 Hz, Ar-H).

Provenance & Evidence