Phosphorus sulfide (P2S5) → 7-Chloro-2,3-dihydro-5-phenyl-2-thioxo-1H-1,4-benzodiazepin-1-acetic acid methyl ester

HRID 1580608Notes

Reaction equation

HRID 1580608 reaction equation
[CH3:1][O:2][C:3](=[O:24])[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[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:8][CH2:7][C:6]1=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:26]>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:24])[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[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:8][CH2:7][C:6]1=[S:26]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 149939577-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetic acid methyl ester

Product 1

HCID 543695097-Chloro-2,3-dihydro-5-phenyl-2-thioxo-1H-1,4-benzodiazepin-1-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 6.35 g. (0.0186 mole) of 7-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetic acid methyl ester, 4.42 g. (0.0199 mole) of phosphorus pentasulfide and 185 ml. of pyridine is heated under reflux for about 19 hours. The pyridine is evaporated, 100 ml. of cold water is added, and the product is extracted with four 100-ml. portions of methylene chloride. The extracts are combined, washed with sodium bicarbonate solution and saturated salt solution, dried over anhydrous magnesium sulfate and evaporated to give 2.5 g. of residue. The residue thus obtained is extracted with eight 250-ml. portions of boiling ether. The extracts are combined and concentrated. On standing 2.1 g. of 7-chloro-2,3-dihydro-5-phenyl-2-thioxo-1H-1,4-benzodiazepin-1-acetic acid methyl ester of melting point 180°-182° c. crystallizes from solution; recrystallization from ether raises the melting point to 185°-187° C.

Workup

  1. additionA mixture of 6.35 g
  2. temperatureunder reflux for about 19 hours
  3. customThe pyridine is evaporated
  4. additionof cold water is added
  5. extractionthe product is extracted with four 100-ml
  6. washwashed with sodium bicarbonate solution and saturated salt solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated
  9. customto give 2.5 g
  10. customThe residue thus obtained
  11. extractionis extracted with eight 250-ml
  12. concentrationconcentrated
  13. customcrystallizes from solution
  14. customrecrystallization from ether
  15. temperatureraises the melting point to 185°-187° C.

Sources & evidence

ORD record
ord-7fc2ffd0c9dd4ace943405876e158625
Source dataset
uspto-grants-1976_01
Patent number
US03933816

Reaction notes

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