Sodium hydride → HCID 59497289, compound

HRID 1747291Notes

Reaction equation

HRID 1747291 reaction equation
[C:1]1([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[NH:14][C:13]2=[O:21])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:25][C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=1)[C:29]([O:31][CH3:32])=[O:30]>CN(C=O)C.C(OCC)(=O)C>[CH3:32][O:31][C:29](=[O:30])[C:28]1[CH:33]=[CH:34][CH:35]=[C:26]([CH2:25][N:14]2[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:12]([CH2:11][C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[C:13]2=[O:21])[CH:27]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 517981Methyl 3-(bromomethyl)benzoateHCID 24071726HCID 24071726, compound

Product 1

HCID 59497289HCID 59497289, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-Naphthalen-1-ylmethyl-1,3-dihydro-benzimidazol-2-one (0.1 g, 0.37 mmol) in DMF (3 mL) was added 60% NaH (22 mg, 0.55 mmol). The reaction mixture was stirred at room temperature for 10 min and then Methyl 3-(bromomethyl)benzoate (0.1 g, 0.44 mmol) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 2 h. When the reaction was complete, the mixture was diluted with ethyl acetate and washed with water (×4). The organic phase was then dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 100% CH2Cl2 as an elunet to afford 0.14 g of the desired product as a white foam. LCMS (ESMS): m/z 423.84 (M+H+).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 h
  2. washwashed with water (×4)
  3. dry with materialThe organic phase was then dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-95b5619cd9a84783ba721e91d0c636bf
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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