Phosphorus sulfide (P2S5) → HCID 135848419, compound

HRID 262982Notes

Reaction equation

HRID 262982 reaction equation
[Cl:1][C:2]1[S:18][C:5]2[NH:6][C:7](=O)[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:20].C(=O)(O)[O-].[Na+]>COCCOCCOC>[Cl:1][C:2]1[S:18][C:5]2[NH:6][C:7](=[S:20])[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 135624489HCID 135624489, compound

Product 1

HCID 135848419HCID 135848419, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
75 °C

Procedure

1.5 g (0.00545 mol) of 7-chloro-1,3-dihydro-5-phenyl-2H-thieno[2,3-e]-1,4-diazepin-2-one are suspended in 40 ml of diethyleneglycol dimethyl ether, warmed to 75° C. with stirring and a mixture of 2.2 g of phosphorus pentasulphide and 1.5 g of sodium bicarbonate, which has been finely triturated, is added. The mixture is stirred for a further hour and the solvent is removed under vacuum. The remaining oil is treated with ice and water, the crystalline residue filtered under a vacuum and washed with a large amount of water. The precipitate is suspended in 150 ml of water and shaken out five times with 100 ml of methylene chloride each time. After drying over sodium sulphate, the organic phase is evaporated and the crystalline residue recrystallized from absolute methanol to yield 7-chloro-1,3-dihydro-5-phenyl-2H-thieno[2,3-e]-1,4-diazepine-2-thione which melts at 223°-225° C. (decomposition).

Workup

  1. customhas been finely triturated
  2. additionis added
  3. stirringThe mixture is stirred for a further hour
  4. customthe solvent is removed under vacuum
  5. additionThe remaining oil is treated with ice and water
  6. filtrationthe crystalline residue filtered under a vacuum
  7. washwashed with a large amount of water
  8. stirringshaken out five times with 100 ml of methylene chloride each time
  9. dry with materialAfter drying over sodium sulphate
  10. customthe organic phase is evaporated
  11. customthe crystalline residue recrystallized from absolute methanol

Sources & evidence

ORD record
ord-014ae2bcc82d4715a72ef63d1cee0840
Source dataset
uspto-grants-1979_05
Patent number
US04155913

Reaction notes

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