Lawesson's reagent → (11aS)-1,2,3,10,11,11a-Hexahydro-5H-Pyrrolo[2,1-c][1,4]Benzodiazepin-5-Thione

HRID 1976234Notes

Reaction equation

HRID 1976234 reaction equation
[CH2:1]1[C@H:5]2[CH2:6][NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10](=O)[N:4]2[CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:25])=CC=1>C1(C)C=CC=CC=1>[CH2:1]1[C@H:5]2[CH2:6][NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10](=[S:25])[N:4]2[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 44430444(11aS)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

Product 1

HCID 59954341(11aS)-1,2,3,10,11,11a-Hexahydro-5H-Pyrrolo[2,1-c][1,4]Benzodiazepin-5-ThioneYield 73.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 50 ml of toluene, there were added 2.02 g of (11aS)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one prepared in Reference Example 24 and 4.04 g of the Lawesson's reagent and the mixture was heated under reflux for one hour. After cooling the reaction solution, it was concentrated. The resulting residue was subjected to silica gel column chromatography and then eluted with chloroform/acetone (99/1). The elute was concentrated and recrystallized from ethyl acetate to give 1.6 g (yield 73.3%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one hour
  3. temperatureAfter cooling the reaction solution, it
  4. concentrationwas concentrated
  5. washeluted with chloroform/acetone (99/1)
  6. concentrationThe elute was concentrated
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0c14b74fd6654ae39b5cd20b0be7797a
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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