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

HRID 1287566Notes

Reaction equation

HRID 1287566 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 diluted with 250 ml. of water. The reaction mixture is extracted three times with benzene. The combined benzene layers are washed twice 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. additiondiluted with 250 ml
  4. extractionThe reaction mixture is extracted three times with benzene
  5. washThe combined benzene layers are washed twice with water
  6. concentrationconcentrated
  7. customto remove the solvent
  8. customThe residue is recrystallized from ethyl acetate yielding the pure dextrorotatory isomer

Sources & evidence

ORD record
ord-fa327d4847364d9aaf7e868e193a0a68
Source dataset
uspto-grants-1976_10
Patent number
US03985732

Reaction notes

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