Potassium Carbonate → HCID 10904393, compound

HRID 1290701Notes

Reaction equation

HRID 1290701 reaction equation
[O:1]=[C:2]1[CH2:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[NH:3]1.[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:3]2[C:4]3[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=3[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:7][CH2:8][C:2]2=[O:1])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 76175RO-05-2921

Product 1

HCID 10904393HCID 10904393, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine (13.43 g, 57 mmmol, prepared as described by Mark G. Bock et al in Journal of Organic Chemistry, Vol. 52, pp. 3232-3239, year 1987), 4-methoxybenzyl chloride (12.6 mL, 62.5 mmol) and potassium carbonate (15.7 g, 114 mmol) in N,N-dimethylformamide (130 mL) was heated at 60° C. overnight under an atmosphere of argon. The resultant slurry was concentrated and the residue was treated with ethyl acetate and water. The organic extract was separated, washed twice with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuo. The residue was subjected to column chromatography on silica gel eluting with 1:1 ethyl acetate and hexane. Collection and concentration of appropriate fractions provided 2,3-dihydro-1-[4-methoxybenzyl]-2-oxo-5-phenyl-1H-1,4-benzodiazepine.

Workup

  1. customprepared
  2. concentrationThe resultant slurry was concentrated
  3. additionthe residue was treated with ethyl acetate and water
  4. extractionThe organic extract
  5. customwas separated
  6. washwashed twice with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuo
  10. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-ebdec12ed064421b8aa3fe4a0f8ade56
Source dataset
uspto-grants-1998_05
Patent number
US05753650

Reaction notes

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