Sodium hydride → HCID 66957227, compound

Participants

Reaction Steps

Ring closure of alcohol 143 with NaH (1.5 equiv.) as in Example 2AA, followed by chromatography of the product on silica gel, eluting with 0-33% EtOAc/petroleum ether (foreruns) and then with 0-5% EtOAc/CH2Cl2, gave 7-[(4-iodophenoxy)methyl]-7-methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (144) (74%) as a pale yellow solid: mp (CH2Cl2/hexane) 170-172° C.; 1H NMR (CDCl3) δ 7.57 (dt, J=9.0, 2.7 Hz, 2H), 7.44 (s, 1H), 6.64 (dt, J=9.0, 2.7 Hz, 2H), 4.19-4.05 (m, 2H), 4.07 (d, J=9.6 Hz, 1H), 4.02 (d, J=9.6 Hz, 1H), 2.49 (ddd, J=14.5, 7.4, 6.0 Hz, 1H), 2.24 (ddd, J=14.5, 6.4, 5.9 Hz, 1H), 1.58 (s, 3H). Anal. (C14H14IN3O4) C, H, N.

Provenance & Evidence