Sodium hydride → Ammonium Hydroxide

HRID 458540Notes

Reaction equation

HRID 458540 reaction equation
[C:1]1([C:7]2[CH:11]=[N:10][C:9](=[O:12])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>O>[NH4+:8].[OH-:12].[O:12]=[C:9]1[NH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:11][N:10]1[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 19875228HCID 19875228, compound

Product 2

HCID 14923Ammonium HydroxideHCID 86606173HCID 86606173, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-phenylimidazol-2-one (1.00 g, 6.24 mmol) in DMP (10 mL) at 0° C. was added sodium hydride (300 mg of a 60% dispersion in mineral oil, 7.49 mmol). The mixture was stirred at 0° C. for 1 h, then tert-butyl bromoacetate (1.47 g, 7.49 mmol) was added. The reaction mixture was allowed to warn to ambient temperature and stirring was continued for 18 h. The reaction mixture was poured into water and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give a crude product, which was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH:NH4OH—100:0:0 to 90:5:0.5 to provide the title compound. MS: m/z=275 (M+1).

Workup

  1. customto warn to ambient temperature
  2. stirringstirring
  3. waitwas continued for 18 h
  4. extractionextracted with CH2Cl2 (3×)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a crude product, which
  9. customwas purified by silica gel chromatography
  10. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-3b120cce8b604bc38a54617b3ce3901d
Source dataset
uspto-grants-2007_03
Patent number
US07192954B2

Reaction notes

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