Imidazole → HCID 58964311, compound

HRID 1362952Notes

Reaction equation

HRID 1362952 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].[C:10]([Si:14](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1>C1COCC1>[C:10]([Si:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[O:9][C:3]1[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=1[NH2:1])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 915912-Amino-5-chlorophenolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 58964311HCID 58964311, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-5-chlorophenol (0.949 g, 6.61 mmol), tert-butylchlorodiphenylsilane (2.50 mL, 9.61 mmol), and imidazole (1.335 g, 19.6 mmol) were dissolved in THF (50 mL). Several days later, the reaction mixture was concentrated to give an oil which was purified by SiO2 column chromatography (eluent: 45% dichloromethane/55% hexanes). The product was dried ill vacuo to afford 2-(tert-butyl-diphenyl-silanyloxy)-4-chloro-phenylamine as a yellow oil (784.2 mg, 31%). 1H NMR (400 MHz, DMSO-d6) δ: 7.72-7.64 (m, 4H), 7.55-7.43 (m, 6H), 6.71 (d, J=8.45 Hz, 1H), 6.65 (dd, J=8.46, 2.27 Hz, 1H), 6.10 (d, J=2.26 Hz, 1H), 1.05 (s, 9H).

Workup

  1. concentrationSeveral days later, the reaction mixture was concentrated
  2. customto give an oil which
  3. customwas purified by SiO2 column chromatography (eluent: 45% dichloromethane/55% hexanes)
  4. customThe product was dried ill vacuo

Sources & evidence

ORD record
ord-0d1ef17ff9e34df89857a60b60470761
Source dataset
uspto-grants-2011_02
Patent number
US07884101B2

Reaction notes

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