Sodium hydride → HCID 70795677, compound

HRID 2066619Notes

Reaction equation

HRID 2066619 reaction equation
Cl[C:2]1[N:3]([CH2:10][CH:11]([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][CH:11]2[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

3

Reactant 2

HCID 24758Sodium hydrideHCID 66956527HCID 66956527, compound

Product 1

HCID 70795677HCID 70795677, compoundYield 77%

Procedure

Ring closure of alcohol 84 with NaH as in Example 2A at 0° C. for 80 min and then at 17° C. for 60 min, followed by chromatography of the product on silica gel, eluting with 0-40% EtOAc/petroleum ether (foreruns) and then with 40% EtOAc/petroleum ether and 0-0.5% MeOH/CH2Cl2, gave 2-[(4-iodophenoxy)methyl]-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazole (85) (77%) as a pale yellow solid: mp (MeOH/CH2Cl2/hexane) 198-199° C.; 1H NMR [(CD3)2SO] δ 8.15 (s, 1H), 7.61 (dt, J=8.9, 2.6 Hz, 2H), 6.80 (dt, J=9.0, 2.6 Hz, 2H), 5.72 (m, 1H), 4.49 (dd, J=10.7, 9.0 Hz, 1H), 4.41 (dd, J=11.6, 2.7 Hz, 1H), 4.35 (dd, J=11.6, 5.2 Hz, 1H), 4.20 (dd, J=10.8, 6.5 Hz, 1H). Anal. (C12H10IN3O4) C, H, N.

Workup

  1. customat 0° C.
  2. customfor 80 min
  3. washeluting with 0-40% EtOAc/petroleum ether (foreruns)

Sources & evidence

ORD record
ord-a2369a00e0674a088dbb67cad6ff5972
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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