Sodium hydride → HCID 66957191, compound

Participants

Reaction Steps

Ring closure of alcohol 175 with NaH as in Example 2GGG for 5 h, followed by chromatography of the product on silica gel, eluting with 0-1% EtOAc/CH2Cl2 (foreruns) and then with 1.5-2% EtOAc/CH2Cl2, gave 6-[(4-iodophenoxy)methyl]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (176) (78%) as a pale yellow solid: mp (CH2Cl2/pentane triturate) 239-240° C.; 1H NMR [(CD3)2SO] δ 8.09 (s, 1H), 7.60 (dt, J=9.0, 2.7 Hz, 2H), 6.82 (dt, J=9.0, 2.7 Hz, 2H), 4.59 (dd, J=10.9, 2.9 Hz, 1H), 4.44 (dd, J=11.0, 7.2 Hz, 1H), 4.28 (dd, J=12.5, 5.4 Hz, 1H), 4.09 (dd. J=10.0, 6.7 Hz, 1H), 4.06 (dd, J=10.0, 6.7 Hz, 1H), 4.03 (dd, J=12.5, 7.0 Hz, 1H), 2.82 (m, 1H). Anal. (C13H12IN3O4) C, H, N.

Provenance & Evidence