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

HRID 1287571Notes

Reaction equation

HRID 1287571 reaction equation
[CH3:1][NH:2][C:3]1[C:4](=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:5]([N:7]1[CH2:11][CH2:10][CH:9]=[CH:8]1)=[O:6].[O:16]1CCC[CH2:17]1>>[CH3:1][N:2]1[C:3]2[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=2[C:5](=[O:6])[N:7]2[CH2:11][CH2:10][CH2:9][CH:8]2[C:17]1=[O:16]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 131710479HCID 131710479, compound

Product 1

HCID 985943610-methyl-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione

Procedure

A mixture of 24.8 g. of racemic 1-(N-methylanthraniloyl)pyroline and 21 g. of dicyclohexylcarbonyl diimide in 300 ml. of tetrahydrofuran is stirred at room temperature for 24 hours and then heated on the steam bath for 4 hours. The reaction mixture is filtered to remove the insoluble dicyclohexyl urea and the mother liquid is concentrated to recover the desired product, which is further purified by recrystallization from ethyl acetate.

Workup

  1. additionA mixture of 24.8 g
  2. temperatureheated on the steam bath for 4 hours
  3. filtrationThe reaction mixture is filtered
  4. customto remove the insoluble dicyclohexyl urea
  5. concentrationthe mother liquid is concentrated
  6. customto recover the desired product, which
  7. customis further purified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-e98a77f1764649d585edbb00272de046
Source dataset
uspto-grants-1976_10
Patent number
US03985732

Reaction notes

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