Methyl iodide → 10-methyl-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione

HRID 917963Notes

Reaction equation

HRID 917963 reaction equation
[CH2:1]1[CH:5]2[C:6](=[O:16])[NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10](=[O:11])[N:4]2[CH2:3][CH2:2]1.[CH3:17][O-].[Na+].CI>C(O)C>[CH3:17][N:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10](=[O:11])[N:4]2[CH2:3][CH2:2][CH2:1][CH:5]2[C:6]1=[O:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5511392,3-Dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11ah)-dioneHCID 10942334Sodium Methoxide

Product 1

HCID 985943610-methyl-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.32 g. of 1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c] [1,4]benzodiazepin-5,11(10H)-dione, 1.2 g. of sodium methylate and 40 ml. of ethanol is stirred at room temperature for 3 houRS and 3 ml. of methyl iodide is added. The reaction mixture is stirred for 6 hours longer and concentrated. The residue is mixed with benzene and water and the layers are separated. The benzene layer is washed with water and concentrated. The product is further purified by recrystallization from ethyl acetate and melts at 124°-126°C.

Workup

  1. additionA mixture of 4.32 g
  2. concentrationconcentrated
  3. additionThe residue is mixed with benzene and water
  4. customthe layers are separated
  5. washThe benzene layer is washed with water
  6. concentrationconcentrated
  7. customThe product is further purified by recrystallization from ethyl acetate and melts at 124°-126°C.

Sources & evidence

ORD record
ord-6b2abe0808bb49e1a7cd5970cd31c038
Source dataset
uspto-grants-1976_07
Patent number
US03968230

Reaction notes

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