Water → HCID 14392498, compound

HRID 1382145Notes

Reaction equation

HRID 1382145 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[C:11]([N:15]2[C:19](=[O:20])[N:18]([CH:21]([F:23])[F:22])[C:17]([CH3:24])=[N:16]2)=[CH:10][C:3]=1[O:4][CH:5]([CH3:9])[C:6]([OH:8])=[O:7].[N+:25]([CH:28]([CH3:31])[CH2:29]O)([O-:27])=[O:26].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1.C(OCC)C>[Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[C:11]([N:15]2[C:19](=[O:20])[N:18]([CH:21]([F:23])[F:22])[C:17]([CH3:24])=[N:16]2)=[CH:10][C:3]=1[O:4][CH:5]([CH3:9])[C:6]([O:8][CH2:29][CH:28]([N+:25]([O-:27])=[O:26])[CH3:31])=[O:7]

Participants

7

Reactant 4

HCID 962WaterHCID 921872-Nitropropan-1-olHCID 521998p-Toluenesulfonic acid monohydrateHCID 13769405HCID 13769405, compound2×

Product 1

HCID 14392498HCID 14392498, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A stirred mixture of 0.5 g (0.0013 mole) of 2-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionic acid (Compound A1), 1.0 g (0.0095 mole) of 2-nitro-1-propanol and 0.05 g (0.0003 mole) of p-toluenesulfonic acid monohydrate in 60 mL of toluene was heated at reflux. The water generated in the reaction was removed by collection in a Dean-Stark trap. After refluxing for a total of two hours, the solvent was removed by distillation under reduced pressure leaving a residue. This residue was dissolved in diethyl ether and washed first with water then with an aqueous 10% sodium hydroxide solution. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to yield 0.5 g of 2-nitropropyl 2-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionate as an oil, Compound B1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customwas removed by collection in a Dean-Stark trap
  4. temperatureAfter refluxing for a total of two hours
  5. customthe solvent was removed by distillation under reduced pressure
  6. customleaving a residue
  7. washwashed first with water
  8. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-a2d0bec0e7a245c4bbf91de726faf577
Source dataset
uspto-grants-1989_02
Patent number
US04806145

Reaction notes

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