Phosphorus sulfide (P2S5) → 7-Chloro-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-thione

HRID 371634Notes

Reaction equation

HRID 371634 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3=[CH:12][S:13][CH:14]=[C:9]3[C:8](=O)[NH:7][C:6]=2[CH:16]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:18]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3=[CH:12][S:13][CH:14]=[C:9]3[C:8](=[S:18])[NH:7][C:6]=2[CH:16]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 6195267-Chloro-5,10-dihydrothieno[3,4-b][1,5]benzodiazepin-4-one

Product 1

HCID 125216547-Chloro-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-thione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.88 g. of 7-chloro-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and 1.0 g. of phosphorus pentasulfide in 10 ml. of dry pyridine is stirred and heated under reflux for 4 hours. The mixture is concentrated to dryness and the residue is stirred in 20 ml. of 1 N sodium carbonate solution (pH 7-7.2) for 18 hours. The precipitate is collected, washed with water and recrystallized from methanol-water to give a deep yellow solid, m.p. 197°-198.5° C. (dec.).

Workup

  1. additionA mixture of 0.88 g
  2. temperatureheated
  3. temperatureunder reflux for 4 hours
  4. concentrationThe mixture is concentrated to dryness
  5. customThe precipitate is collected
  6. washwashed with water
  7. customrecrystallized from methanol-water
  8. customto give a deep yellow solid, m.p. 197°-198.5° C. (dec.)

Sources & evidence

ORD record
ord-57c6bcf612234e049bf57b22791d1310
Source dataset
uspto-grants-1978_05
Patent number
US04087421

Reaction notes

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