Phosphorus sulfide (P2S5) → HCID 135848421, compound

HRID 262974Notes

Reaction equation

HRID 262974 reaction equation
[Cl:1][C:2]1[S:21][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][C:12]=3[N+:17]([O-:19])=[O:18])[C:4]=2[CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:23]>N1C=CC=CC=1>[Cl:1][C:2]1[S:21][C:5]2[NH:6][C:7](=[S:23])[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N+:17]([O-:19])=[O:18])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 135848420HCID 135848420, compound

Product 1

HCID 135848421HCID 135848421, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1 g (0.00327 mol) of 7-chloro-1,3-dihydro-5-(o-nitrophenyl)-2H-thieno[2,3-e]-1,4-diazepin-2-one are heated to reflux with 0.8 g of phosphorus pentasulphide in 30 ml of absolute pyridine, nitrogen being conducted through the solution. The mixture is separated on a column (φ3 cm) filled with 50 g of Silica gel[(0.05 to 0.2 mm) (Merck)] (the product travelling on the front and the impurities travelling only slowly). After concentration of the pyridine solution under a vacuum, the residue is treated with methylene chloride and brought to crystallization. After completion of the crystallization in a refrigerator, the mixture is filtered under a vacuum and washed with a small amount of ice-cold methylene chloride. Recrystallization from absolute methanol yields 7-chloro-1,3-dihydro-5-(o-nitrophenyl)-2H-thieno[2,3-e]-1,4-diazepine-2-thione in the form of yellow crystals, melting point 213°-215° C.

Workup

  1. customThe mixture is separated on a column (φ3 cm)
  2. additionfilled with 50 g of Silica gel[(0.05 to 0.2 mm) (Merck)] (the product travelling on the front
  3. additionAfter concentration of the pyridine solution under a vacuum, the residue is treated with methylene chloride
  4. custombrought to crystallization
  5. customAfter completion of the crystallization in a refrigerator
  6. filtrationthe mixture is filtered under a vacuum
  7. washwashed with a small amount of ice-cold methylene chloride
  8. customRecrystallization from absolute methanol

Sources & evidence

ORD record
ord-a324a1fa704640bd8acab8df8995123b
Source dataset
uspto-grants-1979_05
Patent number
US04155913

Reaction notes

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