Sodium hydride → (4-t-butylbenzyl)thiocarbamic acid-O-(3,5-dimethylpyrazol-1-ylmethyl)ester

HRID 656308Notes

Reaction equation

HRID 656308 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH2:8][OH:9])[N:3]=1.[H-].[Na+].[C:12]([C:16]1[CH:25]=[CH:24][C:19]([CH2:20][N:21]=[C:22]=[S:23])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]>O1CCCC1>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH2:8][O:9][C:22](=[S:23])[NH:21][CH2:20][C:19]2[CH:24]=[CH:25][C:16]([C:12]([CH3:14])([CH3:13])[CH3:15])=[CH:17][CH:18]=2)[N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 963933,5-Dimethylpyrazol-1-methanolHCID 148010411-Tert-butyl-4-(isothiocyanatomethyl)benzene

Product 1

HCID 59087970(4-t-butylbenzyl)thiocarbamic acid-O-(3,5-dimethylpyrazol-1-ylmethyl)esterYield 48.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,5-dimethylpyrazol-1-methanol 33-3 (200 mg) and sodium hydride (42 mg) were dissolved in anhydrous tetrahydrofuran (20 ml) and the solution was stirred for 1 hour. To the solution was added 4-t-butylbenzylisothiocyanate (330 mg) and the mixture was stirred at room temperature for 12 hours. The resulting mixture was filtered under reduced pressure and the solvent was removed therefrom. The residue was purified by column-chromatography (ethyl acetate/hexane=1/2) to yield the compound 33-4 (253 mg, 48%) as a solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. filtrationThe resulting mixture was filtered under reduced pressure
  3. customthe solvent was removed
  4. customThe residue was purified by column-chromatography (ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-242ec50fab224ca091000489e26ecb0a
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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