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

HRID 917962Notes

Reaction equation

HRID 917962 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[CH3:9][N:10]1C(=O)O[C:13](=[O:14])[C:12]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:11]12.CS(C)=O>O>[CH3:9][N:10]1[C:11]2[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=2[C:13](=[O:14])[N:1]2[CH2:8][CH2:7][CH2:6][CH:2]2[C:3]1=[O:5]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 25160N-Methylisatoic anhydrideHCID 145742L-Proline

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 962WaterSolvent

Procedure

A mixture of 12.3 g. of L-proline, 17.7 g. of N-methyl isatoic anhydride and 100 ml. of dimethyl sulfoxide is heated on a steam bath for 6 hours, cooled and then dilted with 250 ml. of water. The reaction mixture is extracted three times with benzene. The combined benzene layers are washed with water and concentrated to remove the solvent. The residue is recrystallized from ethyl acetate yielding the pure dextrorotatory isomer.

Workup

  1. additionA mixture of 12.3 g
  2. temperaturecooled
  3. extractionThe reaction mixture is extracted three times with benzene
  4. washThe combined benzene layers are washed with water
  5. concentrationconcentrated
  6. customto remove the solvent
  7. customThe residue is recrystallized from ethyl acetate yielding the pure dextrorotatory isomer

Sources & evidence

ORD record
ord-2114c81e27f54293ad16cbd45d9a4b7b
Source dataset
uspto-grants-1976_07
Patent number
US03968230

Reaction notes

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