Hydrochloric Acid → HCID 19882827, compound

HRID 846515Notes

Reaction equation

HRID 846515 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[C:11]([N:15]2[C:19](=[O:20])[N:18]([CH2:21][CH2:22][CH3:23])[N:17]=[N:16]2)=[CH:10][C:3]=1[O:4][CH2:5][C:6]([O:8]C)=[O:7].[OH-].[Na+].Cl>CO.O>[Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[C:11]([N:15]2[C:19](=[O:20])[N:18]([CH2:21][CH2:22][CH3:23])[N:17]=[N:16]2)=[CH:10][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54064609HCID 54064609, compound2×

Product 1

HCID 19882827HCID 19882827, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A stirred solution of 0.5 g (0.0014 mole) of methyl 2,4-dichloro-5-(1,4-dihydro-5-oxo-4-propyltetrazol-1-yl)phenoxyacetate (compound 83) and 0.08 g (0.0021 mole) of sodium hydroxide in 10 mL of methanol was heated at reflux temperature for 1.5 hours. The reaction mixture was cooled, then evaporated under reduced pressure to leave a solid residue. The residue was dissolved in 20 mL of water, and the solution acidified with concentrated hydrochloric acid. A solid precipitate formed and was collected by filtration and washed with cold water. Recrystallization from diethyl ether:pentane provided 0.2 g of 2,4-dichloro-5-[1,4-dihydro-5-oxo-4-propyltetrazol-1-yl)phenoxyacetic acid, mp 134°-136° C.

Workup

  1. temperatureat reflux temperature for 1.5 hours
  2. temperatureThe reaction mixture was cooled
  3. customevaporated under reduced pressure
  4. customto leave a solid residue
  5. customA solid precipitate formed
  6. filtrationwas collected by filtration
  7. washwashed with cold water
  8. customRecrystallization from diethyl ether

Sources & evidence

ORD record
ord-94f6f3635a254ef9a385c6f082a8588b
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

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