Water → 2-(5-Nitro-2-(2-methoxyethoxy)phenyl)-5-phenylbenzoxazole

HRID 722525Notes

Reaction equation

HRID 722525 reaction equation
[H-].[Na+].F[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[C:13]1[O:14][C:15]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:18][C:16]=2[N:17]=1.[OH2:28]>COC(O)C>[N+:10]([C:7]1[CH:8]=[CH:9][C:4]([O:28][CH2:5][CH2:13][O:14][CH3:15])=[C:5]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:18][C:16]=3[N:17]=2)[CH:6]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 218843342-(2-Fluoro-5-nitrophenyl)-5-phenylbenzoxazole

Product 1

HCID 218844502-(5-Nitro-2-(2-methoxyethoxy)phenyl)-5-phenylbenzoxazoleYield 79%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Procedure

Sodium hydride (30 mg, 1.2 mmol) was added portionwise to a stirred suspension of 2-(2-fluoro-5-nitrophenyl)-5-phenylbenzoxazole (200 mg, 0.6 mmol) in methoxyethanol (2 ml) at 0° C. When gas evolution had visibly ceased the mixture was allowed to warm to room temperature and then heated at 55° C. for 3 h. After being allowed to cool to room temperature the mixture was diluted with water (5 ml) and extracted with EtOAc (3×5 ml). The combined organic extracts were washed with brine (5 ml), dried (Na2SO4) and evaporated under reduced pressure to give the subtitle compound (186 mg, 79%). 1H NMR (DMSO) δ 8.90(d, 1H), 8.45(dd, 1H), 8.10(d, 1H), 7.85(d, 1H), 7.77(m, 3H), 7.52(m, 3H), 7.41(t, 1H), 4.50(t, 2H), 4.84(t, 2H), 3.40(s, 3H).

Workup

  1. temperatureheated at 55° C. for 3 h
  2. temperatureto cool to room temperature the mixture
  3. extractionextracted with EtOAc (3×5 ml)
  4. washThe combined organic extracts were washed with brine (5 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ba263dc5cee444cbad10e39e8d43e44b
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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