HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → 2-({[4-(Benzyloxy)benzyl]oxy}methyl)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 1-{[4-(benzyloxy)benzyl]oxy}-3-(2-bromo-4-nitro-1H-imidazol-1-yl)-2-methyl-2-propanol | HCID 66956082 | — |
| Product | 2-({[4-(Benzyloxy)benzyl]oxy}methyl)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazole | HCID 50913633 | 97% |
Reaction Steps
Ring closure of alcohol 126 with NaH (1.5 equiv.) as in Example 2A for 80 min, followed by chromatography of the product on silica gel, eluting with CH2Cl2, gave 26 (97%) as a cream solid: mp (CH2Cl2/hexane) 130-131° C.; 1H NMR (CDCl3) δ 7.48 (s, 1H), 7.45-7.29 (m, 5H), 7.16 (dt, J=8.7, 2.4 Hz, 2H), 6.94 (dt, J=8.7, 2.4 Hz, 2H), 5.06 (s, 2H), 4.52 (d, J=11.7 Hz, 1H), 4.47 (d, J=11.7 Hz, 1H), 4.32 (d, J=10.0 Hz, 1H), 3.86 (d, J=10.0 Hz, 1H), 3.67 (d, J=10.6 Hz, 1H), 3.53 (d, J=10.6 Hz, 1H), 1.62 (s, 3H). Anal. (C21H21N3O5) C, H, N.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08293734B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-1b1ce8a13836494cbe3fc1e5c9f6f5fb |
| Source note | uspto-grants-2012_10 |