Imidazole → HCID 70231076, compound

HRID 1978033Notes

Reaction equation

HRID 1978033 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH:11]=[CH:12][CH2:13][OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CN=C1.[CH3:20][C:21]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])[CH3:22].O>ClCCl>[CH3:20][C:21]([Si:24]([CH3:26])([CH3:25])[O:14][CH2:13][CH:12]=[CH:11][S:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 53678505HCID 53678505, compound

Product 1

HCID 70231076HCID 70231076, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of a 1.5 to 1 mixture of (E) and (Z) 3-(4-nitrophenylthio)-2-propenol (3.53 g, 16.71 mmol) (JCS, Perkin Trans. I, 1974, 25) in dichloromethane (40 mL) was treated with imidazole (2.28 g, 33.4 mmol) and TBDMSCl (2.77 g, 18.4 mmol), stirred at room temperature for 24 hours, and then partioned between dichloromethane and water. The organic phase was dried, concentrated, and purified on silica gel by flash column chromatography eluting with 8 to 1 hexanes/ethyl acetate to give 5.1 g (94%) of the desired product. Rf: 0.8 (2:1 hexane:ethyl acetate)

Workup

  1. customThe organic phase was dried
  2. concentrationconcentrated
  3. custompurified on silica gel by flash column chromatography
  4. washeluting with 8 to 1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-b85afa8cec6e41e28b8ac2b4e088bdb7
Source dataset
uspto-grants-2001_05
Patent number
US06235786B1

Reaction notes

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