Phosphorus sulfide (P2S5) → HCID 24104717, compound

HRID 1076200Notes

Reaction equation

HRID 1076200 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7](=O)[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[NH:10][C:4]=2[CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:19]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7](=[S:19])[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[NH:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 215392327-chloro-5H-dibenzo[b,e][1,4]diazepin-11(10H)-one

Product 1

HCID 24104717HCID 24104717, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 7-chloro-5,10-dihydro-11H-dibenzo[b,e]-[1,4]diazepin-11-one (30.5 g., 0.125 mole), phosphorus pentasulfide (27.8 g., 0.131 mole) and one l. of pyridine is heated at reflux temperature for 4 hours and the pyridine is evaporated in vacuo. The residue is stirred for 1 hour with one l. each of saturated aqueous sodium bicarbonate and methylene chloride and filtered to remove some solid product. The organic layer of the filtrate is washed successively with sodium bicarbonate solution and with saturated salt solution, dried over anhydrous magnesium sulfate and evaporated. The residue is combined with the solid obtained above and triturated with hot chloroform and methanol. In this way, 12.2 g. of 7-chloro-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepine-11-thione of melting point 274°-275° C is obtained. Concentration of the chloroform-methanol washings affords an additional 8.4 g. of product having the same melting point. Recrystallization from dimethylformamide-water gives an analytically pure sample in the form of pale yellow needles of melting point 276°-277° C.

Workup

  1. temperatureat reflux temperature for 4 hours
  2. customthe pyridine is evaporated in vacuo
  3. filtrationeach of saturated aqueous sodium bicarbonate and methylene chloride and filtered
  4. customto remove some solid product
  5. washThe organic layer of the filtrate is washed successively with sodium bicarbonate solution and with saturated salt solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customobtained above and
  9. customtriturated with hot chloroform and methanol

Sources & evidence

ORD record
ord-9fa84ab32dff40238aeac1361602e05b
Source dataset
uspto-grants-1976_05
Patent number
US03956297

Reaction notes

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