Sodium hydride → HCID 10298465, compound

HRID 1828606Notes

Reaction equation

HRID 1828606 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:12]([CH3:21])[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1.[H-].[Na+].C(=O)(O)[O-].[Na+]>C1(O)CCCCC1.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([C:22]([O:24][CH:25]2[CH2:4][CH2:3][CH2:2][CH2:7][CH2:26]2)=[O:23])[N:12]([CH3:21])[C:13]=1[C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 10179718HCID 10179718, compound

Product 1

HCID 10298465HCID 10298465, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7966CyclohexanolSolvent

Procedure

To a solution of ethyl 4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-1-methylimidazole-2-carboxylate (28 mg, 0.07 mmol) from Example 36, Step A (Method B) in cyclohexanol (2 mL) and methylene chloride (1 mL) was added a catalytic amount of sodium hydride (60% in mineral oil, <5 mg). The mixture was stirred at rt for 2 hr and then poured into aq. sodium bicarbonate and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by Prep TLC (3×1 mm, silica) (25% ethyl acetate in hexanes) to afford the title compound. HPLC/MS: 463 (M+1), 465 (M+3); Rt=4.50 min.

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 Prep TLC (3×1 mm, silica) (25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c84cd04b890d458287fb2f211969d9fd
Source dataset
uspto-grants-2006_06
Patent number
US07057051B2

Reaction notes

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