Octanoic acid, 2-acetyl-8-(2-chloro-4-methoxyphenoxy)-, ethyl ester → HCID 178492574, compound

HRID 224507Notes

Reaction equation

HRID 224507 reaction equation
[C:1]([CH:4]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[Cl:25])[C:5](OCC)=[O:6])(=O)[CH3:2].[NH2:26][NH:27]C(N)=S.C[O-].[Na+]>CO>[Cl:25][C:18]1[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:17]=1[O:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:4]1[C:5]([OH:6])=[N:26][NH:27][C:1]=1[CH3:2]

Participants

5

Reactant 3

HCID 514183Octanoic acid, 2-acetyl-8-(2-chloro-4-methoxyphenoxy)-, ethyl esterHCID 2723789ThiosemicarbazideHCID 10942334Sodium Methoxide

Product 1

HCID 178492574HCID 178492574, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 11.1 g (0.03 m) of ethyl 2-acetyl-8-(2-chloro-4-methoxyphenoxy)octanoate, 2.73 g (0.03 m) of thiosemicarbazide and 1.62 g (0.03 m) of sodium methoxide in 15 ml of methanol was heated at reflux for 24 hours. The solid product was collected, washed with 50% aqueous ethanol and recrystallized from ethanol to give 5.6 g of 4-[6-(2-chloro-4-methoxyphenoxy)hexyl]-5-methyl-1H-pyrazol-3-ol, m.p. 145°-146° C.; MIC=6 microg/ml (herpes 2). (During this reaction the thiocarbamyl group (CSNH2) of the thiosemicarbazide was cleaved so that the reaction product is the same as that obtained when unsubstituted hydrazine is used.)

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. customThe solid product was collected
  4. washwashed with 50% aqueous ethanol
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-da33f3904bda42978dd1bbbcab80d562
Source dataset
uspto-grants-1980_11
Patent number
US04232161

Reaction notes

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