Phosphorus sulfide (P2S5) → HCID 20360389, compound

HRID 1580642Notes

Reaction equation

HRID 1580642 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=O)[CH2:9][N:8]=[C:7]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[F:20])[C:6]=2[CH:21]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:23]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[S:23])[CH2:9][N:8]=[C:7]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[F:20])[C:6]=2[CH:21]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 232757631,4-BENZDIAZEPIN-2-ONE-5(26F-PH)7CL

Product 1

HCID 20360389HCID 20360389, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 7.65 g. (0.025 mole) of 1,3-dihydro-7-chloro-5-(2,6-difluorophenyl)-2H-1,4-benzodiazepin-2-one in 500 ml. of pyridine is treated with 5.55 g. (0.025 mole) of phosphorus pentasulfide and heated under reflux in a nitrogen atmosphere for two hours. The pyridine (350 ml.) is removed in vacuo and the thus-produced residue is poured onto crushed ice. The aqueous phase is extracted with methylene chloride and then discarded. The extract is washed successively with three 200-ml. portions of water and 100 ml. of brine, and dried over anhydrous sodium sulfate. Removal of the solvent gives 7.0 g. of solid which is recrystallized from ethanol-water, to give in 2 crops, 6.8 g. of crude material which, after recrystallization from ethanolwater, gives pure 1,3-dihydro-7-chloro-5-(2,6-difluorophenyl)-2H-1,4-benzodiazepine-2-thione, m.p. 222.5°-224° C.

Workup

  1. temperatureunder reflux in a nitrogen atmosphere for two hours
  2. customThe pyridine (350 ml.) is removed in vacuo
  3. additionthe thus-produced residue is poured
  4. customonto crushed ice
  5. extractionThe aqueous phase is extracted with methylene chloride
  6. washThe extract is washed successively with three 200-ml
  7. dry with materialof brine, and dried over anhydrous sodium sulfate
  8. customRemoval of the solvent
  9. customgives 7.0 g
  10. customof solid which is recrystallized from ethanol-water
  11. customto give in 2 crops, 6.8 g
  12. customof crude material which, after recrystallization from ethanolwater

Sources & evidence

ORD record
ord-114b5d30a6514178b7a154c1f92649be
Source dataset
uspto-grants-1976_01
Patent number
US03933794

Reaction notes

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