Sodium hydride → HCID 66955584, compound

HRID 2066627Notes

Reaction equation

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

Participants

Reactant 2

HCID 24758Sodium hydride

HCID 66956468HCID 66956468, compound

Product 1

HCID 66955584HCID 66955584, compoundYield 92%

Procedure

Ring closure of alcohol 99 with NaH as in Example 2A for 75 min, followed by chromatography of the product on silica gel, eluting with CH2Cl2, gave 2-[(4-iodophenoxy)methyl]-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazole (100) (92%) as a cream solid: mp (MeOH/CH2Cl2/hexane) 181-183° C.; 1H NMR (CDCl3) δ 7.57 (dt, J=9.0, 2.7 Hz, 2H), 7.54 (s, 1H), 6.63 (dt, J=9.0, 2.7 Hz, 2H), 4.46 (d, J=10.2 Hz, 1H), 4.20 (d, J=10.1 Hz, 1H), 4.05 (d, J=9.9 Hz, 1H), 4.03 (d, J=10.1 Hz, 1H), 1.78 (s, 3H). Anal. (C13H12IN3O4) C, H, N.

Workup

customfor 75 min
washeluting with CH2Cl2

Sources & evidence

ORD record: ord-3936c9498c104820b5eba40c0b27edc5
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293734B2

Reaction notes

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