Methyl iodide → HCID 67087785, compound

HRID 2175689Notes

Reaction equation

HRID 2175689 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:11]=[CH:12]/[C:13]([N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[NH:17][C:16]2=[O:24])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].IC.[C:27]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:11]=[CH:12]/[C:13]([N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]([CH3:27])[C:16]2=[O:24])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67889876HCID 67889876, compound

Product 1

HCID 67087785HCID 67087785, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (E)-1-(3-(3,4-dimethoxyphenyl)acryloyl)-1H-benzo[d]imidazol-2(3H)-one (240 mg, 0.75 mmol), iodomethane (68 uL, 1.1 mmol) and K2CO3 (204 mg, 1.5 mmol) in DMF (5 mL) was stirred at room temperature overnight. The reaction was quenched with water and extracted with DCM. The combined organic phases were washed with brine, dried over sodium sulfate and the solvent removed under reduced pressure. The residue was purified by recrystallisation from EtOH to afford (E)-1-(3-(3,4-dimethoxyphenyl)acryloyl)-3-methyl-1H-benzo[d]imidazol-2(3H)-one (200 mg, 79%). 1H-NMR (400 MHz, CDCl3) δ 3.46 (s, 3H), 3.96 (s, 3H), 3.98 (s, 3H), 6.91 (d, J=8.4 Hz, 1H), 7.01 (dd, J=7.6, 0.8 Hz, 1H), 7.19-7.28 (m, 4H), 7.98 (d, J=15.6 Hz, 1H), 8.15 (d, J=15.6 Hz, 1H) 8.32 (dd, J=8.0, 0.8 Hz, 1H); LC-MS (ES-API); rt 9.05 min; m/z calculated for C19H18N2O4 [M+H]+ 339.1, found 339.0 and 361.0 ([M+Na]+).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with DCM
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed under reduced pressure
  6. customThe residue was purified by recrystallisation from EtOH

Sources & evidence

ORD record
ord-831c0c2a73234fb4998561660f302207
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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