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

HRID 890672Notes

Reaction equation

HRID 890672 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-02038aa5d4a14067aef012d61033217c
Source dataset
uspto-grants-2006_02
Patent number
US06998412B2

Reaction notes

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