Phosphorus sulfide (P2S5) → 2-Methyl-5,10-dihydro-4H-thieno[2,3-b][1,5]benzodiazepine-4-thione

HRID 131303Notes

Reaction equation

HRID 131303 reaction equation
[CH3:1][C:2]1[S:11][C:10]2[NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5](=O)[C:4]=2[CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:18].C(O)C.O>N1C=CC=CC=1>[CH3:1][C:2]1[S:11][C:10]2[NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5](=[S:18])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 19096565Water ethanolHCID 29978685LY-301664

Product 1

HCID 210935012-Methyl-5,10-dihydro-4H-thieno[2,3-b][1,5]benzodiazepine-4-thioneYield 71.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Combine 2-methyl-4,9-dihydro-3-thia-4,9-diazabenzo[f]azulene-10-one (21 g, 0.09 mol) and phosphorus pentasulfide (53 g, 0.12 mol) in pyridine (350 mL) and stir at room temperature overnight, heat at reflux for 5 h. Cool to room temperature to allow precipitate to settle, collect solid by filtration, wash cake with cold ethanol/water and air-dry for a few minutes to obtain 29 g of crude material. Take up solid in a small amount of pyridine, add a like volume of ethanol/water, sonicate for a few minutes and collect again by filtration. Air-dry cake, then place in the vacuum oven at 40° C. for 48 h to obtain 15.9 g of the title compound as an orange solid, which was used directly on the next step without further purification: melting point: 259.0-259.5° C.; Mass spectrum (APCI): m/z=247.0 (M+1).

Workup

  1. temperatureheat
  2. temperatureat reflux for 5 h
  3. customcollect solid
  4. filtrationby filtration
  5. washwash cake with cold ethanol/water
  6. customair-dry for a few minutes
  7. customto obtain 29 g of crude material
  8. customsonicate for a few minutes
  9. filtrationcollect again by filtration
  10. customAir-dry cake

Sources & evidence

ORD record
ord-2807434eacc64f3ea2257fa824211620
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

Loading…