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Imidazole → HCID 20735497, compound

HRID 723621
Notes
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Reaction equation

HRID 723621 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:12][N:13]([CH2:17][CH2:18][OH:19])[C:14]=2[CH2:15][CH3:16])[CH:5]=[C:6]([Cl:8])[CH:7]=1.N1C=CN=C1.[C:30]([Si:34]([CH3:37])([CH3:36])Cl)([CH3:33])([CH3:32])[CH3:31]>CN(C)C=O>[Si:34]([O:19][CH2:18][CH2:17][N:13]1[C:14]([CH2:15][CH3:16])=[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:12]1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:37])[CH3:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10200330Ethyl 4-[(3,5-dichlorophenyl)sulfanyl]-5-ethyl-1-(2-hydroxyethyl)-1H-pyrazole-3-carboxylate

Product 1

HCID 20735497HCID 20735497, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 46 (1.03 g, 2.65 mmol) in dimethylformamide (5 ml) was added imidazole (361 mg, 5.30 mmol), followed by tert-butyldimethylchlorosilane (600 mg, 3.97 mmol). The solution was stirred at room temperature for 4 days. The reaction mixture was partitioned between ethyl acetate and water and the aqueous phase was further extracted with ethyl acetate. The combined organic phases were dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give a yellow oil. The crude product was purified by flash chromatography on silica gel eluting with cyclohexane:ethyl acetate (20:1, by volume), followed by cyclohexane:ethyl actetate (5:1, by volume) to afford the title compound (1.1 g) as a white powder, m.p. 83–84° C.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionthe aqueous phase was further extracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give a yellow oil
  7. customThe crude product was purified by flash chromatography on silica gel eluting with cyclohexane:ethyl acetate (20:1, by volume)

Sources & evidence

ORD record
ord-6b078e2f5cae49bdac380bedbb392213
Source dataset
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07141585B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes