HCID 21290714, compound → HCID 21290694, compound

HRID 623214Notes

Reaction equation

HRID 623214 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([CH2:8][NH:9][C:10](=[O:15])[CH2:11][O:12][CH2:13][CH3:14])=O)=[CH:4][CH:3]=1>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]2[O:15][C:10]([CH2:11][O:12][CH2:13][CH3:14])=[N:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 21290714HCID 21290714, compound

Product 1

HCID 21290694HCID 21290694, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

12.78 g (50 mmol) of N-[(4-chlorobenzoyl)methyl]-2-ethoxyacetamide were dissolved in 32.5 ml of concentrated sulphuric acid while stirring and cooling intermittently so that the temperature did not rise above room temperature. The mixture was held at room temperature for 20 hours, then poured on to 600 ml of ice/water and extracted three times with 150 ml of diethyl ether each time. The combined ether extracts were washed with 100 ml of saturated sodium hydrogen carbonate solution, then dried over magnesium sulphate, filtered and evaporated to give 10.55 g (89%) of 5-(4-chlorophenyl)-2-ethoxymethyloxazole in the form of a syrup.

Workup

  1. temperaturecooling intermittently so that the temperature
  2. customdid not rise above room temperature
  3. extractionextracted three times with 150 ml of diethyl ether each time
  4. washThe combined ether extracts were washed with 100 ml of saturated sodium hydrogen carbonate solution
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e9a4627388d742f2bae7195fcadebc31
Source dataset
uspto-grants-1988_09
Patent number
US04774253

Reaction notes

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