1-Chloromethylnaphthalene → HCID 59497422, compound

HRID 1747300Notes

Reaction equation

HRID 1747300 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:10]=2[NH:9][C:8]1=[O:18])[CH3:2].Cl[CH2:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:10]=2[N:9]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)[C:8]1=[O:18])[CH3:2]

Participants

6

Reactant 3

HCID 68451-ChloromethylnaphthaleneHCID 11430Potassium CarbonateHCID 59497687HCID 59497687, compound

Product 1

HCID 59497422HCID 59497422, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 3-(6-Cyano-2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid ethyl ester (0.1 g, 0.39 mmol) in DMA (3 mL) were added 1-(chloromethyl)naphthalene (0.1 g, 0.58 mmol) and K2CO3 (0.11 g, 0.81 mmol). The reaction mixture was stirred at 65° C. for 16 h. When the reaction was complete, the reaction mixture was diluted with ethyl acetate and washed with water (×4). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 98:2 CH2Cl2:MeOH as an eluent to afford 20 mg (13%) of the desired product.

Workup

  1. washwashed with water (×4)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-ce743809a1ed48fc87b037e112392ac8
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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