Sodium hydride → HCID 22419172, compound

HRID 1720571Notes

Reaction equation

HRID 1720571 reaction equation
[CH2:1]([C:5]1[NH:9][C:8]2[C:10](=[O:17])[C:11]([CH3:16])=[C:12]([CH3:15])[C:13](=[O:14])[C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[C:20]([O:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[CH:38]=[CH:37][C:36]([CH2:39]Br)=[CH:35][CH:34]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21].[Cl-].[NH4+]>CN(C)C=O>[C:20]([O:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[CH:38]=[CH:37][C:36]([CH2:39][N:9]2[C:8]3[C:10](=[O:17])[C:11]([CH3:16])=[C:12]([CH3:15])[C:13](=[O:14])[C:7]=3[N:6]=[C:5]2[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:35][CH:34]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 15294065HCID 15294065, compound

Product 1

HCID 22419172HCID 22419172, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

340 mg (1.5 mmol) Of the benzimidazol-4,7-dione was dissolved in 15 ml of dimehtylformarnide, and this was cooled to 0° C. After 65 mg (1.6 mmol) of 60% sodium hydride was added and the mixture was stirred for 30 min. A solution of 503 mg (1.5 mmol) of (2'-t-butoxycarbonylbiphenyl-4-yl)methyl bromide in 2 ml of dimethylformamide was added dropwise and the mixture was stirred for 1 hour. To the reaction mixture was added an aqueous saturated solution of ammonium chloride, and this was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, and this was dried over anhydrous sodium sulphate, and the solvent was distilled off under the reduced pressure. The resultant crude product was purified by silica gel chromatography (ethyl acetate: n-hexane=5:1) to obtain 421 mg of 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-n-butyl-5,6-dimethyl-1H-benzimidazol-4,7-dione as yellow oily material (Yield 58%). This has the following NMR spectrum. δ ppm (CDCl3): 0.91 (3H, t, J=7 Hz), 1.21 (9H, s), 1.35-1.43 (H, s), 1.76-1.82 (2H, m), 2.04 (3H, s), 2.10 (3H, s), 5.62 (2H, s), 7.10 (2H, d, J=8 Hz), 7.27-7.30 (3H, m), 7.39-7.42 (1H, m), 7.45-7.48 (1H, m), 7.78 (1H, dd, J=6, 1 Hz)

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. extractionthis was extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  4. dry with materialthis was dried over anhydrous sodium sulphate
  5. distillationthe solvent was distilled off under the reduced pressure
  6. customThe resultant crude product was purified by silica gel chromatography (ethyl acetate: n-hexane=5:1)

Sources & evidence

ORD record
ord-9b6c6d4239424a0cb9b36b244abb42bf
Source dataset
uspto-grants-1996_04
Patent number
US05506361

Reaction notes

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