Sodium hydride → HCID 57678299, compound

HRID 491413Notes

Reaction equation

HRID 491413 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]1.[H-].[Na+].Br[CH2:11][C:12]([NH2:14])=[O:13]>C1COCC1.CN(C=O)C>[CH:6]([C:4]1[N:3]=[CH:2][N:1]([CH2:11][C:12]([NH2:14])=[O:13])[CH:5]=1)=[O:7]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 764281H-Imidazole-4-carbaldehyde

Product 1

HCID 57678299HCID 57678299, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1H-imidazole-4-carbaldehyde (1.92 g, 20 mmol) in anhydrous THF (32 mL) and DMF (8 mL) was treated with sodium hydride (60% dispersion in mineral oil, 880 mg, 22 mmol) for 5 mins. 2-Bromoacetamide (3.59 g, 26 mmol) was added and the reaction was stirred continuously overnight. The THF was concentrated, loaded on a silica column, and eluted with 20% methanol in dichloromethane. The solvent was evaporated to yield 2.70 g of the product as a white solid (88.2%). HPLC Method D, r.t.=1.5 min, (96.4% purity at 256 nm). LC/MS calculated mass=153.14, [M−H]−=152, [M+H]+=154.

Workup

  1. concentrationThe THF was concentrated
  2. washeluted with 20% methanol in dichloromethane
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b88bef526dd94b58847c53fbe2c1dde1
Source dataset
uspto-grants-2009_05
Patent number
US07531542B2

Reaction notes

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