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

HRID 1287565Notes

Reaction equation

HRID 1287565 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 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-methylanthraniloyl)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-methylanthraniloyl)proline, melting point 140°-142° C., [α]D25 -165° C. (1.1%, methanol)

Sources & evidence

ORD record
ord-be3315b4147b4d9790ff1618f6d636b3
Source dataset
uspto-grants-1976_10
Patent number
US03985732

Reaction notes

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