Phosphorus sulfide (P2S5) → HCID 21525533, compound

HRID 1658768Notes

Reaction equation

HRID 1658768 reaction equation
[CH3:1][N:2]([CH2:4][C:5]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10](=O)[C:9]2[CH:19]=[CH:20][CH:21]=[N:22][C:8]1=2)=[O:6])[CH3:3].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:24]>N1C=CC=CC=1>[CH3:1][N:2]([CH2:4][C:5]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10](=[S:24])[C:9]2[CH:19]=[CH:20][CH:21]=[N:22][C:8]1=2)=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 21525543HCID 21525543, compound

Product 1

HCID 21525533HCID 21525533, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 6,11-dihydro-11-[(dimethylamino)acetyl]-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one (0.14 mole), phosphorus pentasulfide (0.155 mole) and 1200 ml. of pyridine is heated at reflux temperature for 24 hours and the pyridine is then evaporated. Methylene chloride and water are added, and the organic layer is separated (some solid is present), washed with aqueous sodium bicarbonate until only a trace of solid is present, then with saturated salt solution, dried over anhydrous magnesium sulfate and evaporated. Trituration of the residue with methanol gives a solid which after crystallization from methylene chloride-methanol gives the product 6,11-dihydro-11-[(dimethylamino)acetyl]-5H-pyrido[2,3-b][1,5]benzodiazepin-5-thione.

Workup

  1. temperatureat reflux temperature for 24 hours
  2. customthe pyridine is then evaporated
  3. additionMethylene chloride and water are added
  4. customthe organic layer is separated (some solid
  5. washwashed with aqueous sodium bicarbonate until only a trace of solid
  6. dry with materialwith saturated salt solution, dried over anhydrous magnesium sulfate
  7. customevaporated
  8. customTrituration of the residue with methanol gives a solid which
  9. customafter crystallization from methylene chloride-methanol

Sources & evidence

ORD record
ord-be93c92d01774eed9da7d1b38534317c
Source dataset
uspto-grants-1976_06
Patent number
US03966736

Reaction notes

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