Sodium Sulfide → HCID 23196366, compound

HRID 726531Notes

Reaction equation

HRID 726531 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([N+:21]([O-:23])=[O:22])=[CH:13][C:12]=1[N+:24]([O-])=O)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[OH-].[NH4+].[Cl-].[NH4+].[S-2].[Na+].[Na+]>C(O)C.O>[CH2:1]([O:3][P:4]([CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([N+:21]([O-:23])=[O:22])=[CH:13][C:12]=1[NH2:24])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

7

Reactant 4

HCID 14804Sodium SulfideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 57269183HCID 57269183, compound

Product 1

HCID 23196366HCID 23196366, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.352 g of (2,4 dinitro-1-naphthylamino)-methanephosphonic acid diethyl ester is dissolved in 32 ml of ethanol and 23 ml of water, to it is added 4.4 ml of 25% ammonium hydroxide solution, 1.61 g of ammonium chloride and 2.81 g of 35% sodium sulfide and the solution is heated for a few hours to 90° C. The ethanol-water mixture is concentrated by evaporation on a rotary evaporator, taken up in water, extracted with ethyl acetate, washed with brine, dried and spun in. The crude product is chromatographed on silica gel with 2 liters of cyclohexane and ethyl acetate 1:1 and 1 liter of pure ethyl acetate as mobile solvent. 262 mg of product is obtained in several fractions as brown solid.

Workup

  1. temperaturethe solution is heated for a few hours to 90° C
  2. concentrationThe ethanol-water mixture is concentrated by evaporation on a rotary evaporator
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. customdried
  6. customThe crude product is chromatographed on silica gel with 2 liters of cyclohexane and ethyl acetate 1:1 and 1 liter of pure ethyl acetate as mobile solvent

Sources & evidence

ORD record
ord-064072076a9c4cafa8a912a57c44549f
Source dataset
uspto-grants-1998_01
Patent number
US05710138

Reaction notes

Loading…