Chloromethyl Methyl Ether → HCID 21201664, compound

HRID 1979289Notes

Reaction equation

HRID 1979289 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:4][CH2:3]1.[H-].[Na+].[CH3:21][O:22][CH2:23]Cl>O1CCCC1>[CH3:21][O:22][CH2:23][N:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:4][CH2:3][C:2]1=[O:1]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 16640186HCID 16640186, compound

Product 1

HCID 21201664HCID 21201664, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In an argon stream, 2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (40.4 g) was added to 60% sodium hydride (8.84 g) suspended in absolute tetrahydrofuran (500 ml) at 0° C. The mixture was stirred for one hour at 0° C., and chloromethyl methyl ether (20.5 g) was added thereto, followed by stirring for two hours and 30 minutes at room temperature. The reaction mixture was concentrated under reduced pressure, and ice-water was added thereto, followed by extraction with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, to thereby obtain 47.4 g of the title compound as a yellow oil (yield: 98.8%).

Workup

  1. stirringby stirring for two hours and 30 minutes at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and ice-water
  3. additionwas added
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-929cba91cd534189b7635e2ccf779b73
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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