Sodium hydride → HCID 17952493, compound

HRID 1828180Notes

Reaction equation

HRID 1828180 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][C:13](=[O:21])[C:14]3[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=3)=[CH:11][C:6]=2[N:5]([CH2:22][CH3:23])[C:4]1=[O:24])[CH3:2].[H-].[Na+].Br[CH2:28][C:29]([C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)=[O:30]>CN(C)C(=O)C>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]([CH2:28][C:29]([C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)=[O:30])[C:13]([C:14]3[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=3)=[O:21])=[CH:11][C:6]=2[N:5]([CH2:22][CH3:23])[C:4]1=[O:24])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1514083-(2-Bromoacetyl)pyridineHCID 22063798HCID 22063798, compound

Product 1

HCID 17952493HCID 17952493, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

To a cooled (0° C.) solution of 1,3-diethyl-5-(2-oxo-2-m-tolyl-ethyl)-1,3-dihydro-benzoimidazol-2-one (prepared as described previously, 500 mg, 1.55 mmol) in N,N-dimethylacetamide (DMA, 2.35 mL) was added NaH (124 mg of a 60% dispersion in mineral oil, 3.1 mmol). The slurry was stirred for 10 minutes, then a solution of 3-(Bromoacetyl)pyridine (310 mg, 1.55 mmol) in DMA (0.470 mL) was added. After 1 hour, the reaction was quenched with 3 mL of acetic acid and diluted with water. The aqueous was extracted with EtOAc (3×10 mL), the organics combined and washed with water, saturated sodium bicarbonate, then again with water. The organics were dried over anhydrous sodium sulfate and concentrated in vacuo to afford 600 mg of the title compound.

Workup

  1. customprepared
  2. waitAfter 1 hour
  3. customthe reaction was quenched with 3 mL of acetic acid
  4. additiondiluted with water
  5. extractionThe aqueous was extracted with EtOAc (3×10 mL)
  6. washwashed with water, saturated sodium bicarbonate
  7. dry with materialThe organics were dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b91715f108af43679ad39bf09a6ba32e
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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