Acetic Acid → HCID 14800319, compound

HRID 258094Notes

Reaction equation

HRID 258094 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:12][CH:13]1[N:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[NH:15][C:14]1=[O:30])=[O:11].[H-].[Na+].[CH3:33][O:34][CH2:35][CH2:36]Cl.C(O)(=O)C>CN(C)C=O.O.C(OCC)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:12][CH:13]1[N:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[N:15]([CH2:36][CH2:35][O:34][CH3:33])[C:14]1=[O:30])=[O:11]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydrideHCID 14208192HCID 14208192, compound

Product 1

HCID 14800319HCID 14800319, compoundYield 24.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-2H-1, 4-benzodiazepine-2-one (394 mg) in N,N-dimethylformamide (4 ml) was added sodium hydride (62% suspension in mineral oil, 44 mg) under stirring at 0° C. in an ice-bath. The mixture was stirred for 1.0 hour at 0° to -5° C. 2-Methoxyethyl chloride (142 mg) was added thereto. The mixture was stirred for 6.0 hours at 60° to 70° C. and cooled. To the cooled reaction mixture were added acetic acid (0.5 ml), ethyl acetate (40 ml) and water (40 ml) under stirring. The organic layer was separated, washed with an aqueous solution of sodium bicarbonate and water, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel with chloroform as an eluent to give the pure product of (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-1-(2-methoxyethyl)-2H-1, 4-benzodiazepine-2-one (110 mg).

Workup

  1. stirringThe mixture was stirred for 1.0 hour at 0° to -5° C
  2. stirringThe mixture was stirred for 6.0 hours at 60° to 70° C.
  3. temperaturecooled
  4. customTo the cooled reaction mixture
  5. stirringunder stirring
  6. customThe organic layer was separated
  7. washwashed with an aqueous solution of sodium bicarbonate and water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customThe residue was chromatographed on silica gel with chloroform as an eluent

Sources & evidence

ORD record
ord-a807757c0a524ca69c6c10ef2d5f90bc
Source dataset
uspto-grants-1993_11
Patent number
US05264433

Reaction notes

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