Imidazole → HCID 85805408, compound

HRID 1634728Notes

Reaction equation

HRID 1634728 reaction equation
N1C=CN=C1.[Cl:6][C:7]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].[C:16]([Si:20]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)Cl)([CH3:19])([CH3:18])[CH3:17].O>C(Cl)Cl>[Si:20]([O:15][C:13]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[C:7]([Cl:6])[CH:14]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 1853632-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 85805408HCID 85805408, compoundYield 107.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of imidazole (4.28 g, 62.89 mmol) and 2-chloro-4-hydroxybenzaldehyde (8.95 g, 57.16 mmol) in CH2Cl2 (500 ml)was added dropwise a solution of t-butyldiphenylchlorosilane (17.27 g, 62.86 mmol) in CH2Cl2, (200 mL). The solution was stirred overnight at ambient temperature. The mixture was then poured into H2O (500 mL) and the organic layer washed with NaHCO3, H2O, brine, and dried (MgSO4). The solvent was removed in vacuo to provide 24.2 g of the title compound.

Workup

  1. washthe organic layer washed with NaHCO3, H2O, brine
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bcc0b10cd4064ef4ac67e14d2ad93fbe
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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