Phosphorus sulfide (P2S5) → 5-(2-Chlorophenyl)-7-ethyl-1,3-dihydro-2H-thieno[2,3-e]-1,4-diazepine-2-thione

HRID 1606038Notes

Reaction equation

HRID 1606038 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:18]=[C:17]([CH2:19][CH3:20])[S:16][C:10]=2[NH:11][C:12](=O)[CH2:13][N:14]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:18]=[C:17]([CH2:19][CH3:20])[S:16][C:10]=2[NH:11][C:12](=[S:22])[CH2:13][N:14]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 135624512Desmethylclotiazepam

Product 1

HCID 1356675755-(2-Chlorophenyl)-7-ethyl-1,3-dihydro-2H-thieno[2,3-e]-1,4-diazepine-2-thioneYield 136%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

[a] To a solution of 40 g of 5-o-chlorophenyl-7-ethyl-1,2-dihydro-3H-thieno[2,3-e][1,4]diazepin-2-one in 200 ml of pyridine is added 32 g of phosphorus pentasulfide, and the mixture is stirred at 60°C for 1 hour. After allowing to cool, the reaction mixture is poured into 2 liters of ice water with stirring. The precipitate formed is collected with suction filtration and washed with water. The precipitate is dissolved in chloroform, and the solution is washed with a saturated sodium bicarbonate and washed with water. The chloroform layer is dried over sodium sulfate and concentrated in vacuo. The residue is recrystallized from a mixture of ethanol and chloroform to give 31.4 g of 5-o-chlorophenyl-7-ethyl-1,2-dihydro-3H-thieno[2,3-e][1,4]diazepine-2-thione as yellowish crystals melting at 198°-199°C (decomposition).

Workup

  1. temperatureto cool
  2. stirringwith stirring
  3. customThe precipitate formed
  4. filtrationis collected with suction filtration
  5. washwashed with water
  6. dissolutionThe precipitate is dissolved in chloroform
  7. washthe solution is washed with a saturated sodium bicarbonate
  8. washwashed with water
  9. dry with materialThe chloroform layer is dried over sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe residue is recrystallized from a mixture of ethanol and chloroform

Sources & evidence

ORD record
ord-ce37bafd6d024abd9e79faf7aaf97652
Source dataset
uspto-grants-1976_04
Patent number
US03952006

Reaction notes

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