Sodium hydride → HCID 178468918, compound

HRID 967799Notes

Reaction equation

HRID 967799 reaction equation
[C:1]12([O:11][CH2:12][C:13]3[CH:14]=[C:15]([OH:25])[N:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH3:24])[N:17]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Na+].[CH2:28]([O:30][C:31]([C:33]1[CH:34]=[C:35]([N:39]=[C:40]=[O:41])[CH:36]=[CH:37][CH:38]=1)=[O:32])[CH3:29]>C1COCC1>[CH2:28]([O:30][C:31](=[O:32])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([NH:39][C:40]([C:14]2[C:13]([CH2:12][O:11][C:1]34[CH2:8][CH:7]5[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]5)[CH2:2]3)[CH2:10]4)=[N:17][N:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[C:15]=2[OH:25])=[O:41])[CH:34]=1)[CH3:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 589806Ethyl 3-isocyanatobenzoateHCID 178424338HCID 178424338, compound

Product 1

HCID 178468918HCID 178468918, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 5-(adamantan-1-yloxymethyl)-2-o-tolyl-2H-pyrazol-3-ol (160 mg, 0.47 mmol) in anhydrous THF (4 mL) was added to a suspension of sodium hydride (26 mg of 60% dispersion in oil, 0.65 mmol) in THF (2 mL) under a dry argon atmosphere at room temperature. The mixture was stirred for 30 min. and a solution of 3-ethoxycarbonylphenyl isocyanate (99 mg, 0.5 mmol) in THF (1 mL) added. Stirring was continued for 1 h and the mixture partitioned between 5% KHSO4 (40 mL) and EtOAc (40 mL). The organic phase was washed with brine (30 mL), and dried (MgSO4). Filtration and evaporation of the solvent afforded the product as a red solid, (250 mg, 100%).

Workup

  1. stirringStirring
  2. waitwas continued for 1 h
  3. customthe mixture partitioned between 5% KHSO4 (40 mL) and EtOAc (40 mL)
  4. washThe organic phase was washed with brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-76a00d557fbc4a41b8ef35e4a35239e0
Source dataset
uspto-grants-2005_10
Patent number
US06956053B2

Reaction notes

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