Thiobenzamide → Methyl 2-methyl2-[7-(2-phenyltiazole-4-yl)heptyloxy]propionate

HRID 1794263Notes

Reaction equation

HRID 1794263 reaction equation
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:11][C:12](=O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23]>C(OCC)(=O)C>[CH3:27][C:21]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]1[N:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:8][CH:11]=1)([CH3:26])[C:22]([O:24][CH3:25])=[O:23]

Participants

4

Reactant 2

HCID 683563ThiobenzamideHCID 21866630Methyl 2-(9-chloro-8-oxononyloxy)-2-methylpropionate

Product 1

HCID 131725276Methyl 2-methyl2-[7-(2-phenyltiazole-4-yl)heptyloxy]propionateYield 75.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 783 mg of thiobenzamide and 1.0 g methyl 2-(9-chloro-8-oxononyloxy)-2-methylpropionate were stirred for 2 hours at 120° C. The reaction solution was cooled and dissolved in ethyl acetate, washed by adding sodium hydrogencarbonate, washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=9:1) to provide 963 mg of the objective compound as pale yellow oil.

Workup

  1. temperatureThe reaction solution was cooled
  2. washwashed
  3. additionby adding sodium hydrogencarbonate
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-88b5304d6eb14e99b46e3419d1cb67e3
Source dataset
uspto-grants-2006_04
Patent number
US07022723B2

Reaction notes

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