Phosphorus sulfide (P2S5) → 1,3-dihydro-5-(o-chlorophenyl)-2H-1,4-benzodiazepine-2-thione

HRID 328718Notes

Reaction equation

HRID 328718 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11](=O)[CH2:10][N:9]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[S:21])[CH2:10][N:9]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 145904461,3-Dihydro-5-(2-chlorophenyl)-2H-1,4-benzodiozepin-2-one

Product 1

HCID 125221541,3-dihydro-5-(o-chlorophenyl)-2H-1,4-benzodiazepine-2-thione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 23 g. (0.085 mole) of 1,3-dihydro-5-(o-chlorophenyl)-2H-1,4-benzodiazepin-2-one [Sternbach et al., J. Med. Chem. 6, 261 (1963)] and 21 g. of P2S5 in 1500 ml. of pyridine was heated rapidly to the reflux temperature and refluxed for 45 min. It was then concentrated to dryness in vacuo and the residue was treated with 150 ml. of saturated NaCl solution and extracted (thrice) with methylene chloride. The CH2Cl2 solution was washed (water), dried (MgSO4), filtered and evaporated to dryness. The residue was dissolved in 1 l. of abs EtOH treated with Darco and filtered hot. The solution was then concentrated to 200 ml. and allowed to cool giving 19 g. (78%) of yellow crystalline compound, m.p. 228-229° C. The ir and nmr support the structure.

Workup

  1. additionA mixture of 23 g
  2. temperaturerefluxed for 45 min
  3. concentrationIt was then concentrated to dryness in vacuo
  4. additionthe residue was treated with 150 ml
  5. extractionof saturated NaCl solution and extracted (thrice) with methylene chloride
  6. washThe CH2Cl2 solution was washed (water)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated to dryness
  10. dissolutionThe residue was dissolved in 1 l
  11. additionof abs EtOH treated with Darco
  12. filtrationfiltered hot
  13. concentrationThe solution was then concentrated to 200 ml
  14. temperatureto cool
  15. customgiving 19 g

Sources & evidence

ORD record
ord-e482500244b4470a88029fa4fd1a53f3
Source dataset
uspto-grants-1977_04
Patent number
US04018788

Reaction notes

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