Phosphinic Acid → HCID 57687715, compound

HRID 2194666Notes

Reaction equation

HRID 2194666 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:10]=[C:9]2[S:18][C:19]2[CH:24]=[CH:23][C:22](N)=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.N([O-])=O.[Na+].[PH2](O)=O>Cl.O>[C:5]1([N:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:10]=[C:9]2[S:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 4124402Phosphinic AcidHCID 23668193Sodium NitriteHCID 57687717HCID 57687717, compound

Product 1

HCID 57687715HCID 57687715, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

Ethyl 1-(4-aminophenyl)-2-[(4-aminophenyl)thio]-1H-imidazole-4-carboxylate (1.90 g) was dissolved in concentrated hydrochloric acid (30 mL), and a solution of sodium nitrite (1.00 g) in water (5 mL) was added dropwise at 5-10° C. The mixture was stirred at the same temperature for 1 hr, and the obtained reaction mixture was added dropwise to 50% hypophosphorous acid solution (30 mL) by small portions. The mixture was stirred at room temperature for 3 hr, and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound as a yellow oil (yield 1.17 g, yield 67%).

Workup

  1. customthe obtained reaction mixture
  2. stirringThe mixture was stirred at room temperature for 3 hr
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8cc390478c2740ac98f157d12572f48c
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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