Chloromethyl Methyl Ether → HCID 21201552, compound

HRID 1979332Notes

Reaction equation

HRID 1979332 reaction equation
[H-].[Na+].[O:3]=[C:4]1[NH:10][C:9]2[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:8]=2[N:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:6][CH2:5]1.[CH3:23][O:24][CH2:25]Cl>O1CCCC1>[CH3:23][O:24][CH2:25][N:10]1[C:9]2[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:8]=2[N:7]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:6][CH2:5][C:4]1=[O:3]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 21201698HCID 21201698, compound

Product 1

HCID 21201552HCID 21201552, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon atmosphere, 60% sodium hydride (1.12 g) was suspended in tetrahydrofuran (10 ml), a solution of 2-oxo-5-phenyl-8-methoxy-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (5.0 g) in tetrahydrofuran (50 ml) was added thereto under ice-cooling, and the mixture was stirred for 40 minutes at same temperature. After ice bath was removeded, methoxymethyl chloride (2.25 g) was added, the mixture was stirred for 2 hours at room temperature. The reaction mixture was poured into ice-water, extracted with methylene chloride. The organic layer was successively washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), to thereby obtain 5.05 g of the titled compound as yellow-brown crystals (Yield: 87%).

Workup

  1. temperatureunder ice-cooling
  2. customAfter ice bath was removeded
  3. stirringthe mixture was stirred for 2 hours at room temperature
  4. extractionextracted with methylene chloride
  5. washThe organic layer was successively washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a9fa8918f5064bda81d7a58b1c2ed46d
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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