Triethylamine → Ethyl 2-[4-[6-(2-chloro-4-methoxy-phenoxy)hexyl]-3,5-diethyl-pyrazol-1-yl]acetate

HRID 426784Notes

Reaction equation

HRID 426784 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([C:16](=O)[CH2:17][CH3:18])[C:12](=O)[CH2:13][CH3:14].Cl.[C:27]([CH2:32][NH:33][NH2:34])([O:29][CH2:30][CH3:31])=[O:28].C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:16]([CH2:17][CH3:18])=[N:34][N:33]([CH2:32][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:12]=1[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 41782ArildoneHCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)

Product 1

HCID 6482612Ethyl 2-[4-[6-(2-chloro-4-methoxy-phenoxy)hexyl]-3,5-diethyl-pyrazol-1-yl]acetateYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 18.45 g of 4-[6-(2-chloro-4-methoxyphenoxy)hexyl]-3,5-heptanedione, 7.73 g of carbethoxymethylhydrazine hydrochloride and 5 g of triethylamine in 100 ml of absolute ethanol was heated at reflux for 8 hours. The product was isolated and distilled to give 16.7 g of ethyl 4-[6-(2-chloro-4-methoxyphenoxy)hexyl]-3,5-diethyl-1H-pyrazol-1-acetate as a pale yellow oil, b.p. 205°-210° C. (0.05 mm); MIC=6-12 microg/ml (herpes 1 and 2).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 hours
  3. customThe product was isolated
  4. distillationdistilled

Sources & evidence

ORD record
ord-52885c814fce4684a3c1544b693903b3
Source dataset
uspto-grants-1979_10
Patent number
US04171365

Reaction notes

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