Sodium hydride → HCID 66957227, compound

HRID 2066655Notes

Reaction equation

Cl[C:2]1[N:3]([CH2:10][CH2:11][C:12]([CH3:23])([OH:22])[CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+]>>[I:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][C:12]2([CH3:23])[O:22][C:2]3=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]3[CH2:10][CH2:11]2)=[CH:16][CH:17]=1

Participants

Reactant 2

HCID 24758Sodium hydride

HCID 66956448HCID 66956448, compound

Product 1

HCID 66957227HCID 66957227, compoundYield 74%

Procedure

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.

Workup

washeluting with 0-33% EtOAc/petroleum ether (foreruns)

Sources & evidence

ORD record: ord-6883f10b57c74110a803dec7bdb8fbe3
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293734B2

Reaction notes

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