Sodium hydride → HCID 17981766, compound

HRID 2252042Notes

Reaction equation

HRID 2252042 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1>CN(C=O)C>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N:10]2[CH:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=[CH:9]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 178418822HCID 178418822, compound

Product 1

HCID 17981766HCID 17981766, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-phenylimidazole (7.49 g, 51.9 mmol) in DMF (30 mL) cooled to 0° C. under nitrogen add portionwise NaH (95%, 2.56 g, 101 mmol). After 10 minutes, add p-methoxybenzyl chloride (PMBCl) (7.50 mL, 55.3 mmol) dropwise. Stir for 5 hours, quench with MeOH (5 mL), dilute with water (100 mL), and extract with CH2Cl2 (2×100 mL). Dry the combined organic layers (Na2SO4) and concentrate in vacuo to a volume of 80 mL, affording 12.2 g (89% yield) after crystallization. MS(ES+): m/z=265 (M+H)+

Workup

  1. customquench with MeOH (5 mL)
  2. additiondilute with water (100 mL)
  3. extractionextract with CH2Cl2 (2×100 mL)
  4. dry with materialDry the combined organic layers (Na2SO4)
  5. concentrationconcentrate in vacuo to a volume of 80 mL
  6. customaffording 12.2 g (89% yield)
  7. customafter crystallization

Sources & evidence

ORD record
ord-bd9af531f6bf47cfbffeb465840ef90d
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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