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

HRID 1287569Notes

Reaction equation

HRID 1287569 reaction equation
[CH3:1][NH:2][C:3]1[C:4](=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:5]([N:7]1[CH2:14][CH2:13][CH2:12][C@H:8]1[C:9](O)=[O:10])=[O:6].S(Cl)(Cl)=O>C1C=CC=CC=1>[CH3:1][N:2]1[C:3]2[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=2[C:5](=[O:6])[N:7]2[CH2:14][CH2:13][CH2:12][CH:8]2[C:9]1=[O:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 227914541-[2-(Methylamino)benzoyl]-L-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 241BenzeneSolvent

Procedure

A mixture of 24.8 g. of (-)-1-(N-methylanthraniloyl)-proline and 300 ml. of benzene is stirred and 12.0 g. of thionyl chloride is added dropwise. The mixture is heated at reflux temperature for 2 hours, cooled, washed twice with water and concentrated to recover the (+)-1,2,3,11a-tetrahydro-10-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5,11(10H)-dione.

Workup

  1. additionA mixture of 24.8 g
  2. temperatureThe mixture is heated
  3. temperatureat reflux temperature for 2 hours
  4. temperaturecooled
  5. washwashed twice with water
  6. concentrationconcentrated
  7. customto recover the (+)-1,2,3,11a-tetrahydro-10-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5,11(10H)-dione

Sources & evidence

ORD record
ord-6baa36758e534dc198d9661982ab290f
Source dataset
uspto-grants-1976_10
Patent number
US03985732

Reaction notes

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