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

HRID 1287568Notes

Reaction equation

HRID 1287568 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 16 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-1d61152a66ed46259265c4ee62255df7
Source dataset
uspto-grants-1976_10
Patent number
US03985732

Reaction notes

Loading…