Sodium hydride → HCID 68817764, compound

HRID 735666Notes

Reaction equation

HRID 735666 reaction equation
[H-].[Na+].[N:3]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10])=[C:4]=[O:5].[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[C:17]([O:24][CH2:25][CH3:26])[CH:16]=1>C1COCC1>[C:9]([C:8]1[CH:7]=[C:6]([NH:3][C:4](=[O:5])[O:23][CH2:22][CH2:21][C:18]2[CH:19]=[CH:20][C:15]([Br:14])=[CH:16][C:17]=2[O:24][CH2:25][CH3:26])[CH:13]=[CH:12][CH:11]=1)#[N:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27333153-IsocyanatobenzonitrileHCID 578428372-(4-Bromo-2-ethoxyphenyl)ethan-1-ol

Product 1

HCID 68817764HCID 68817764, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (346 mg, 8.7 mmol, 60% dispersion in oil) was added in one portion to a solution of 3-isocyanatobenzonitrile (567 mmol, 3.9 mmol) and 62E (960 mg, 3.9 mmol) in THF (40 mL) and the cooling bath was removed. After stirring for 2 h at ambient temperature 1.0 N citric acid (50 mL) was added and the mixture was extracted with diethyl ether. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by flash chromatography (0% to 60% EtOAc in hexanes) to yield 62F (611 mg, 50%) as a pale, yellow solid. MS (ESI) m/z 411.0/413.0 (M+H)+.

Workup

  1. customthe cooling bath was removed
  2. additionwas added
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography (0% to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2f00d4618ce74415af3ba3ed1d9f4a62
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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