HCID 15728438, compound → HCID 19863044, compound

HRID 1164715Notes

Reaction equation

HRID 1164715 reaction equation
[Cl:1][C:2]1[C:7]([O:8]C(C)C)=[CH:6][C:5]([N:12]2[C:16](=[O:17])[N:15]([CH2:18][CH2:19][CH2:20][F:21])[C:14]([CH3:22])=[N:13]2)=[C:4]([F:23])[CH:3]=1>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:12]2[C:16](=[O:17])[N:15]([CH2:18][CH2:19][CH2:20][F:21])[C:14]([CH3:22])=[N:13]2)=[C:4]([F:23])[CH:3]=1

Participants

3

Reactant 1

HCID 15728438HCID 15728438, compound

Product 1

HCID 19863044HCID 19863044, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 0.70 g (0.002 mole) of 1-[4-chloro-2-fluoro-5-(1-methylethoxy)phenyl]-4-(3-fluoropropyl)-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one (prepared in Example 1) in 10 mL of concentrated sulfuric acid was stirred for 30 minutes at ambient temperature. The reaction mixture was poured into ice-water and the mixture was extracted with diethyl ether. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 0.5 g of 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-4-(3-fluoropropyl)-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one, which was used immediately in the next step of this reaction sequence.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ce5428e85d264306a6d474fb60b18c4f
Source dataset
uspto-grants-1990_03
Patent number
US04906284

Reaction notes

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