Sodium hydride → HCID 66751577, compound

HRID 2043336Notes

Reaction equation

HRID 2043336 reaction equation
[H-].[Na+].[N:3]1[CH:7]=[C:6]([CH2:8][N:9]([CH:19]([CH3:21])[CH3:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)[NH:5][CH:4]=1.[CH3:22][Si:23]([CH3:30])([CH3:29])[CH2:24][CH2:25][O:26][CH2:27]Cl>O1CCCC1>[CH:19]([N:9]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)[CH2:8][C:6]1[N:5]([CH2:27][O:26][CH2:25][CH2:24][Si:23]([CH3:30])([CH3:29])[CH3:22])[CH:4]=[N:3][CH:7]=1)([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 59728066HCID 59728066, compound

Product 1

HCID 66751577HCID 66751577, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To sodium hydride (149 mg, 55% in mineral oil, 3.42 mmol) in tetrahydrofuran (240 ml) was added a solution of (3H-imidazol-4-ylmethyl)-isopropyl-(3-nitro-phenyl)-amine (685 mg, 2.63 mmol) in tetahydrofuran (100 ml) and stirring was continued for 45 min at room temperature. The reaction mixture was cooled with an ice bath and 2-(trimethylsilyl)ethoxymethylchloride (439 mg, 2.63 mmol) was added. After stirring the suspension overnight the reaction was quenched with saturated sodium bicarbonate solution. Tetrahydrofuran was evaporated and the residue was extracted with ethyl acetate twice. The combined organic layers were washed with water, dried over magnesium sulphate and evaporated. The residue was purified using flash chromatography (SiO2; eluent: heptane/ethyl acetate=80:20) to yield a light yellow oil, (0.20 g, 20%); MS (ISP): 391.3 ((M+H)+.).

Workup

  1. temperatureThe reaction mixture was cooled with an ice bath
  2. stirringAfter stirring the suspension overnight the reaction
  3. customwas quenched with saturated sodium bicarbonate solution
  4. customTetrahydrofuran was evaporated
  5. extractionthe residue was extracted with ethyl acetate twice
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customThe residue was purified
  10. customto yield a light yellow oil, (0.20 g, 20%)

Sources & evidence

ORD record
ord-58d99f90a990470d9c2470362d73fe03
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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