Water → 5-(2-fluorophenyl)-7-nitro-3H-1,4-benzodiazepine-2(1H)-thione

HRID 566291

Reaction equation

HRID 566291 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:13]=2[NH:12][C:11](=O)[CH2:10][N:9]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1.C(=O)([O-])O.[Na+].O>CN(C)P(=O)(N(C)C)N(C)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[S:32])[CH2:10][N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 520217Norflunitrazepam

Product 1

HCID 123714345-(2-fluorophenyl)-7-nitro-3H-1,4-benzodiazepine-2(1H)-thioneYield 183.2%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
105 °C

Procedure

A solution of 20.0 g of 5-(2-fluorophenyl)-7-nitro-3H-1,4-benzodiazepin-2(1H)-one (G. M. Clarke, J. B. Lee, F. J. Swinbourne & B. Williamson, J. Chem. Res. Synop. 1980, 400) in 100 ml of hexamethylphosphoric acid triamide was treated with 14 g of Lawesson reagent and the mixture was stirred at 105° C. for 70 min. The reaction mixture was poured into 800 ml of saturated aqueous sodium hydrogen carbonate solution and 800 ml of water. After stirring at room temperature for 15 min. the precipitate was filtered off, washed with water and dried. There were obtained 20 g of crude 5-(2-fluorophenyl)-7-nitro-3H-1,4-benzodiazepine-2(1H)-thione, which was used in this form for the next step.

Workup

  1. stirringAfter stirring at room temperature for 15 min. the precipitate
  2. filtrationwas filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-431e21bd542f4c30ad9c362f519203d0
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Linked notes

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