Benzamide → HCID 21866859, compound

HRID 857248Notes

Reaction equation

HRID 857248 reaction equation
[C:1]([NH2:9])(=[O: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][O:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22]>C(OCC)(=O)C>[CH3:26][C:20]([O: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)[O:8][CH:11]=1)([CH3:25])[C:21]([O:23][CH3:24])=[O:22]

Participants

4

Reactant 2

HCID 2331BenzamideHCID 21866686HCID 21866686, compound

Product 1

HCID 21866859HCID 21866859, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 956 mg of benzamide and 1.1 g of methyl 2-(8-chloro-7-oxooctyloxy)-2-methylpropionate was stirred for 2 hours at 120° C. The reaction solution was cooled, 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 658 mg of the objective compound as colorless 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-b8fa72443ed7474ea3e9abd02c671cc6
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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