Imidazole → HCID 18475843, compound

HRID 412176Notes

Reaction equation

HRID 412176 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.N1C=CN=C1.[Si:18](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([O:12][Si:18]([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 83588-Amino-2-naphthalenolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 18475843HCID 18475843, compoundYield 360.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-amino-2-naphthol (5.0 g, 31.4 mmol) in 200 mL of dimethylformamide was added imidazole (2.4 g, 34 mmol) and tert-butyldiphenylsilyl chloride (8.6 mL, 33 mmol). After 48 hours, water was added and the reaction was stirred overnight. The solution was partitioned between EtOAc and water, washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to provide the titled product (45.0 g). The crude product was purified by silica gel chromatography (10% EtOAc/hexane) to provide the pure titled product.

Workup

  1. customThe solution was partitioned between EtOAc and water
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb3f85ca299847e8991f6c4643494f78
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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