Sodium Hydroxide → HCID 22114962, compound

HRID 1276129Notes

Reaction equation

HRID 1276129 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:13]([C:14]2[O:18][N:17]=[C:16]([CH:19]([CH3:21])[CH3:20])[N:15]=2)=[C:12]([Cl:22])[CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7]>CO>[Cl:3][C:4]1[C:13]([C:14]2[O:18][N:17]=[C:16]([CH:19]([CH3:20])[CH3:21])[N:15]=2)=[C:12]([Cl:22])[CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 22114902HCID 22114902, compound

Product 1

HCID 22114962HCID 22114962, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2.06 g (51.5 mmol) of sodium hydroxide in 150 ml of methanol were added dropwise to 13.50 g (42.9 mmol) of methyl 2,4-dichloro-3-(3-i-propyl-1,2,4-oxadiazol-5-yl)benzoate in 330 ml of methanol. The mixture was stirred at room temperature for 12 hours and a further 0.52 g (12.9 mmol) of sodium hydroxide were added. The mixture was subsequently stirred at room temperature for a further 48 hours and the solvent was then removed. The residue was taken up in 200 ml of 5% strength potassium carbonate solution and washed once with ethyl acetate and twice with methylene chloride. The aqueous phase that remained was then acidified (pH=2) using hydrochloric acid and extracted repeatedly with methylene chloride. The combined organic phases were dried and concentrated. 7.20 g (56% of theory) of 2,4-dichloro-3-(3-i-propyl-1,2,4-oxadiazol-5-yl)benzoic acid were obtained.

Workup

  1. stirringThe mixture was subsequently stirred at room temperature for a further 48 hours
  2. customthe solvent was then removed
  3. washwashed once with ethyl acetate and twice with methylene chloride
  4. extractionextracted repeatedly with methylene chloride
  5. customThe combined organic phases were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-58af3b1b9aa94b4882476129ad4d332c
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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