Phosphorus sulfide (P2S5) → HCID 135848418, compound

HRID 262977Notes

Reaction equation

HRID 262977 reaction equation
[Cl:1][C:2]1[S:19][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[F:17])[C:4]=2[CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21].C(=O)(O)[O-].[Na+]>COCCOCCOC>[Cl:1][C:2]1[S:19][C:5]2[NH:6][C:7](=[S:21])[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 135848424HCID 135848424, compound

Product 1

HCID 135848418HCID 135848418, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

10 g of 7-chloro-5-(o-fluorophenyl)-1,3-dihydro-2H-thieno[2,3-e]-1,4-diazepin-2-one are dissolved in 150 ml of diethyleneglycol dimethyl ether at 55° C. and stirred with a mixture of 15 g of finely triturated phosphorus pentasulphide and 10 g of sodium bicarbonate for 40 minutes. The solvent is distilled off and the residue washed with water, filtered under vacuum and dried. The 7-chloro-5-(o-fluorophenyl)-1,3-dihydro-2H-thieno[2,3-e]-1,4-diazepine-2-thione thus obtained is refluxed in 200 ml of methanol with 15 g of acetyl hydrazine for 30 minutes. On cooling, 2-(2-acetylhydrazino)-7-chloro-5-(o-fluorophenyl)-3H-thieno[2,3-e]-1,4-diazepine precipitates. The methanol is distilled off and the residue partitioned between methylene chloride and water. The solvent is evaporated under reduced pressure and the residue crystallized from methanol to yield a second crop of 2-(2-acetylhydrazino)-7-chloro-5-(o-fluorophenyl)-3H-thieno[2,3-e]-1,4-diazepine, melting point 207° -209° C.

Workup

  1. distillationThe solvent is distilled off
  2. washthe residue washed with water
  3. filtrationfiltered under vacuum
  4. customdried

Sources & evidence

ORD record
ord-5490f348ae4444e5bb87daad19c4d17d
Source dataset
uspto-grants-1979_05
Patent number
US04155913

Reaction notes

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