Pyridine → HCID 54383478, compound

HRID 1580614Notes

Reaction equation

HRID 1580614 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]([CH3:28])([CH3:27])[N:5]1[C:11]2[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=2[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[N:8][CH:7]([CH2:24][CH3:25])[C:6]1=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:31].N1C=CC=CC=1>C(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:29])[C:4]([CH3:28])([CH3:27])[N:5]1[C:11]2[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=2[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[N:8][CH:7]([CH2:24][CH3:25])[C:6]1=[S:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 14817Phosphorus sulfide (P2S5)HCID 54396852HCID 54396852, compound

Product 1

HCID 54383478HCID 54383478, compound

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

A mixture of 0.01 mole of 7-fluoro-5-(o-chlorophenyl)-2,3-dihydro-α,α-dimethyl-3-ethyl-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 24 hours. The 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. The residue thus obtained is chromatographed on silica gel and eluted to give 7-fluoro-α,α-dimethyl-3-ethyl-5-(o-chlorophenyl)-2,3-dihydro-2-thioxo-1H-1,4-benzodiazepin-1-acetic acid methyl ester.

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe 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. customThe residue thus obtained
  9. customis chromatographed on silica gel
  10. washeluted

Sources & evidence

ORD record
ord-6c26763272d04fc49375b0e3aa54c2ee
Source dataset
uspto-grants-1976_01
Patent number
US03933816

Reaction notes

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