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

HRID 917961Notes

Reaction equation

HRID 917961 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[C:9]12[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:14][C:13](=O)O[C:10]2=[O:11].CS(C)=O>O>[CH3:13][N:14]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=2[C:10](=[O:11])[N:1]2[CH2:8][CH2:7][CH2:6][CH:2]2[C:3]1=[O:5]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8359Isatoic 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-mthyl isatoic anhydride and 100 ml. of dimethyl sulfoxide is heated on a steam bath for 40 minutes. The mixture is cooled and diluted with 250 ml. of cold water. The precipitate is recovered by filtration, washed with water and then ether, air dried and then recrystallized from ethanol yielding the intermediate L-1-(N-methylanthrailoyl)proline, melting point 140°-142°C., [α]D25 -165°C. (1.1%, methanol).

Workup

  1. additionA mixture of 12.3 g
  2. temperatureThe mixture is cooled
  3. additiondiluted with 250 ml
  4. filtrationThe precipitate is recovered by filtration
  5. washwashed with water
  6. dry with materialether, air dried
  7. customrecrystallized from ethanol yielding the intermediate L-1-(N-methylanthrailoyl)proline, melting point 140°-142°C., [α]D25 -165°C. (1.1%, methanol)

Sources & evidence

ORD record
ord-466e381630094c70b4b688924852401d
Source dataset
uspto-grants-1976_07
Patent number
US03968230

Reaction notes

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