Bicarbonate Ion → HCID 22066067, compound

HRID 2101708Notes

Reaction equation

HRID 2101708 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[CH3:20][Si:21]([CH3:28])([CH3:27])[CH2:22][CH2:23][O:24][CH2:25]Cl.[H-].[Na+].C(=O)(O)[O-]>CN(C=O)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:11]=[CH:10][N:9]([CH2:25][O:24][CH2:23][CH2:22][Si:21]([CH3:28])([CH3:27])[CH3:20])[C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 124673074,5-Bis(4-chlorophenyl)-1H-imidazole

Product 1

HCID 22066067HCID 22066067, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4,5-di-(4-chlorophenyl)imidazole (500 mg, 1.7 mmol) from Example 20, Step A and 2-(trimethylsilyl)ethoxymethyl chloride (SEM-Cl) (0.46 mL, 2.6 mmol) in DMF (8 mL) at rt was added sodium hydride (60% in mineral oil) (135 mg, 3.4 mmol). The reaction was stirred for 20 min, poured into an aq. bicarbonate solution, and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by flash chromatography (25% ethyl acetate in hexanes) to afford the title compound as an oil.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by flash chromatography (25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9f35138d43c845148d4ec088d87832a3
Source dataset
uspto-grants-2009_08
Patent number
US07572785B2

Reaction notes

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