Thionyl Chloride → HCID 44478661, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, into a cold (0° C.) solution of (4-tert-butylphenyl)(phenyl)-1,4,5,6,-tetrahydropyrimidin-2-ylmethanol (2.7 g, 8.37 mmol) in CHCl3 was added SOCl2 (1.9 mL) over 10 minutes. The reaction mixture was heated at reflux temperature for 4 h and concentrated in vacuo. The resultant residue was dissolved in benzene and concentrated in vacuo to dryness twice. The final residue was crystallized from chloroform and ether to afford 2-[(4-tert-butyl-phenyl)(chloro)phenylmethyl]-1,4,5,6,-tetrahydropyrimidine as an off white solid (2.4 g, 84% yield, mp 79° C.). MS m/e (M+H)+ 341; 1H NMR (400 MHZ, DMSOd6) δ 1.26 (s, 9H), 1.90 (m, 2H) 3.43 (m, 4H), 7.26 (d, 2H), 7.35 (m, 2H), 7.48 (m, 5H), 9.42 (bs, 1H).

Provenance & Evidence