Sodium Carbonate → HCID 68872130, compound

HRID 2105874Notes

Reaction equation

HRID 2105874 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[NH:11][C:10]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([O:28]CC)=[CH2:27])=[CH:22][C:21]=3[O:31][CH2:32][CH3:33])=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH:12]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[NH:11][C:10]([C:20]3[CH:25]=[CH:24][C:23]([C:26](=[O:28])[CH3:27])=[CH:22][C:21]=3[O:31][CH2:32][CH3:33])=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 68869233HCID 68869233, compound

Product 1

HCID 68872130HCID 68872130, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution of hydrochloric acid (2 M, 18 mL) was sparged for 10 min with nitrogen and then used to slurry 4,5-bis-(4-chlorophenyl)-2-[2-ethoxy-4-(1-ethoxyvinyl)phenyl]-4,5-dihydro-1H-imidazole (0.638 g, 1.33 mmol). Tetrahydrofuran (18 mL) was added to create a homogeneous solution. After stirring 1 h, the reaction mixture was poured into a mixture of 2 M sodium hydroxide (16 mL) and 10% sodium carbonate solution (50 mL) and extracted with methylene chloride (2×100 mL). The combined organic extracts were dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (silica gel, eluting with a gradient of 1-3% methanol in chloroform) to give 1-{4-[4,5-bis-(4-chlorophenyl)-4,5-dihydro-1H-imidazol-2-yl]-3-ethoxyphenyl}ethanone as a faintly yellow foam (0.392 g, 65%). LC-MS: 453.3 [(M+H)+].

Workup

  1. customAn aqueous solution of hydrochloric acid (2 M, 18 mL) was sparged for 10 min with nitrogen
  2. extractionextracted with methylene chloride (2×100 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (silica gel
  6. washeluting with a gradient of 1-3% methanol in chloroform)

Sources & evidence

ORD record
ord-3e01b990b21a499f9ce948be031dac6e
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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