Phosphorus sulfide (P2S5) → HCID 20360389, compound

HRID 1288046Notes

Reaction equation

HRID 1288046 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 was 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.) was removed in vacuo and the thus-produced residue was poured onto crushed ice. The aqueous phase was extracted with methylene chloride and then discarded. The extract was washed successively with three 200-ml. portions of water and 100 ml. of brine, and dried over anhydrous sodium sulfate. Removal of the solvent gave 7.0 g. of solid which was recrystallized from ethanol-water, to give in 2 crops 6.8 g. of crude material which, after recrystallization from ethanol-water, gave pure 1,3-dihydro-7-chloro-5-(2,6-difluorophenyl)-2H-1,4-benzodiazepine-2-thione of melting point 222.5°-224° C.

Workup

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

Sources & evidence

ORD record
ord-6a704f258c974d1ba016075fd15db545
Source dataset
uspto-grants-1976_10
Patent number
US03987052

Reaction notes

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