Phosphorus sulfide (P2S5) → HCID 20361194, compound

HRID 436553Notes

Reaction equation

HRID 436553 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=O)[CH2:10][N:9]=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[C:7]=2[CH:20]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22]>N1C=CC=CC=1>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[S:22])[CH2:10][N:9]=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[C:7]=2[CH:20]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 203612567-(Methylsulfanyl)-5-(pyridin-2-yl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one

Product 1

HCID 20361194HCID 20361194, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred solution of 7-methylthio-1,3-dihydro-5-(2-pyridyl)-2H-1,4-benzodiazepin-2-one (0.0206 mole) in dry pyridine (400 ml.) was treated with phosphorus pentasulfide (5.05 g.), warmed, under nitrogen, at 110°-120° C. for 1 hour, cooled and concentrated in vacuo. Residual pyridine was removed by the successive addition of xylene and toluene to the residue with concentration after each addition. The resulting residue was mixed with dilute sodium carbonate and extracted with chloroform. The chloroform extract was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was crystallized to give 7-methylthio-1,3-dihydro-5-(2-pyridyl)-2H-1,4-benzodiazepine-2-thione.

Workup

  1. temperaturewarmed, under nitrogen, at 110°-120° C. for 1 hour
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. customResidual pyridine was removed by the successive addition of xylene and toluene to the residue with concentration
  5. additionafter each addition
  6. additionThe resulting residue was mixed with dilute sodium carbonate
  7. extractionextracted with chloroform
  8. extractionThe chloroform extract
  9. washwas washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated
  12. customThe residue was crystallized

Sources & evidence

ORD record
ord-604e354abd7b4b1db14869284ed04451
Source dataset
uspto-grants-1977_02
Patent number
US04009175

Reaction notes

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