Pyridine → HCID 54212049, compound

HRID 1580609Notes

Reaction equation

HRID 1580609 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:10]=2[C:9]([C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])=[N:8][CH2:7][C:6]1=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:28].N1C=CC=CC=1>C(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:26])[CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:10]=2[C:9]([C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])=[N:8][CH2:7][C:6]1=[S:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 14817Phosphorus sulfide (P2S5)HCID 54028127HCID 54028127, compound

Product 1

HCID 54212049HCID 54212049, compound

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

A mixture of 0.01 mole of 7-chloro-5-(2,6-difluorophenyl)-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-1-acetic acid methyl ester, 0.0105 mole of phosphorus pentasulfide and 100 ml. of pyridine is heated under reflux for about 24 hours. The reaction mixture is evaporated and the residue thus obtained is dissolved in methylene chloride-water. The organic layer is separated, washed with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate and evaporated to remove the solvent. The residue thus obtained is chromatographed on silica gel and eluted to give 7-chloro-5-(2,6-difluorophenyl)-2,3-dihydro-2-thioxo-1H-1,4-benzodiazepin-1-acetic acid methyl ester.

Workup

  1. temperatureunder reflux for about 24 hours
  2. customThe reaction mixture is evaporated
  3. customthe residue thus obtained
  4. customThe organic layer is separated
  5. washwashed with saturated sodium bicarbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customto remove the solvent
  9. customThe residue thus obtained
  10. customis chromatographed on silica gel
  11. washeluted

Sources & evidence

ORD record
ord-9241d7c0e4cb455292de12491696fbda
Source dataset
uspto-grants-1976_01
Patent number
US03933816

Reaction notes

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