Imidazole → HCID 12007215, compound

HRID 2215805Notes

Reaction equation

HRID 2215805 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][OH:12])([O-:3])=[O:2].N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl>[C:21]([Si:18]([CH3:20])([CH3:19])[O:12][CH2:11][CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 270542-Nitrophenethyl alcoholHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 12007215HCID 12007215, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(2-nitro-phenyl)ethanol (100 g, 590 mmol) in CH2Cl2 (800 mL), was treated with imidazole (117 g, 777 mmol) followed by tert-butyl-dimethylsilylchloride (562 g, 826 mmol). A white precipitate formed upon the addition and the reaction was stirred 2.5 hours. The mixture was filtered and diluted with CH2Cl2 (300 mL) and was washed with 0.1 N HCl (300 mL), H2O (400 mL), saturated aq NaHCO3 (400 mL), and brine (400 mL). The organic layer was dried over MgSO4, filtered and concentrated to give the title compound (160 g, 96%) as a transparent oil. 1H NMR (400 MHz, DMSO-d6) −0.11 (s, 6H), 0.77 (s, 9H), 3.03 (t, J=6 Hz, 2H), 3.79 (t, J=6 Hz), 7.42–7.54 (m, 2H), 7.62 (ddd, J=<1, 6, 7 Hz, 1H), 7.88 (dd, J=<1, 7 Hz, 1H). MS (electrospray, m/z) 282 (H++1).

Workup

  1. customA white precipitate formed upon the addition
  2. filtrationThe mixture was filtered
  3. additiondiluted with CH2Cl2 (300 mL)
  4. washwas washed with 0.1 N HCl (300 mL), H2O (400 mL), saturated aq NaHCO3 (400 mL), and brine (400 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f55ce00172ce4df7ac81d38cca788647
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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