Imidazole → HCID 58964311, compound

HRID 1626178Notes

Reaction equation

HRID 1626178 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 in 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 in vacuo

Sources & evidence

ORD record
ord-0d0284b88fbc454abd7bab6708036156
Source dataset
uspto-grants-2014_07
Patent number
US08785441B2

Reaction notes

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