Imidazole → tert-Butyl-(5-tert-butyl-2-methyl-4-thiocyanato-phenoxy)-dimethyl-silane

HRID 356501Notes

Reaction equation

HRID 356501 reaction equation
[C:1]([C:5]1[C:6]([S:13][C:14]#[N:15])=[CH:7][C:8]([CH3:12])=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.CN(C=O)C.[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>C(=O)(O)[O-].[Na+]>[C:29]([Si:26]([O:11][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]([S:13][C:14]#[N:15])=[CH:7][C:8]=1[CH3:12])([CH3:28])[CH3:27])([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 105609555-tert-Butyl-2-methyl-4-thiocyanato-phenol

Product 1

HCID 18798714tert-Butyl-(5-tert-butyl-2-methyl-4-thiocyanato-phenoxy)-dimethyl-silane

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2.0 g (9.0 mmol) of 5-tert-butyl-2-methyl-4-thiocyanato-phenol (prepared in Example GGG), imidazole (0.800 g, 11.8 mmol) and DMF (10 mL) was treated with t-butyldimethylsilylchloride (1.64 g, 10.9 mmol) and stirred overnight. The mixture was diluted with saturated sodium bicarbonate and the mixture extracted with hexanes. The hexane layers were combined, dried (Na2 SO4), and the solvent removed in vacuo to yield the title compound. 1H NMR (CDCl3) δ 0.23 (s, 6 H), 1.01 (s, 9 H), 1.45 (s, 9 H), 2.16 (s, 3 H), 6.87 (s, 1 H), 7.49 (s, 1 H).

Workup

  1. extractionthe mixture extracted with hexanes
  2. customdried (Na2 SO4)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-55510d6818c742cd954fe61fa6047826
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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