Triethylamine → HCID 22752910, compound

HRID 2163508Notes

Reaction equation

HRID 2163508 reaction equation
[C:1]1([CH2:7][C:8](=[N:10][OH:11])[NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:12][CH:13]([CH3:17])[C:14](Cl)=O.C(N(CC)CC)C>CC(C)=O>[CH2:7]([C:8]1[N:9]=[C:14]([CH:13]([Cl:12])[CH3:17])[O:11][N:10]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1110192-Chloropropionyl chlorideHCID 2731007N'-hydroxy-2-phenylethanimidamide

Product 1

HCID 22752910HCID 22752910, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

First, 15.0 grams (0.1 mole) of phenyl acetamide oxime was combined with 100 milliliters of dry acetone in a 250 milliliter flask fitted with a thermometer and dropping funnel. The solution was stirred and cooled to 0° C. Next, 12.7 grams (0.1 mole) of 2-chloro propionyl chloride and 10.1 grams (0.1 mole) of triethyl amine was added. During the additions, the temperature was maintained at 0 to 5° C. After the additions were complete, the reaction mass was stirred at room temperature for 30 minutes and then was filtered free of salt. The filtrate was evaporated in vacuo at 50° and the residue was taken up in 300 milliliters of toluene. The toluene solution was charged to a 500 milliliter flask fitted with a Dean Stark water trap, 0.1 gram of toluene sulfonic acid was added, and the solution was heated under reflux until water ceased to be evolved. The toluene solution was then treated with activated carbon, filtered and evaporated in vacuo at 50° C. to yield 21.2 grams (95% of theory) of 3-benzyl-5-(1-chloroethyl)1,2,4-oxadiazole. nD30 1.5040.

Workup

  1. customfitted with a thermometer
  2. temperatureDuring the additions, the temperature was maintained at 0 to 5° C
  3. stirringthe reaction mass was stirred at room temperature for 30 minutes
  4. filtrationwas filtered free of salt
  5. customThe filtrate was evaporated in vacuo at 50°
  6. additionThe toluene solution was charged to a 500 milliliter flask
  7. customfitted with a Dean Stark water trap, 0.1 gram of toluene sulfonic acid
  8. additionwas added
  9. temperaturethe solution was heated
  10. temperatureunder reflux until water
  11. additionThe toluene solution was then treated with activated carbon
  12. filtrationfiltered
  13. customevaporated in vacuo at 50° C.

Sources & evidence

ORD record
ord-f0bba99961aa48efbfb51a0739479666
Source dataset
uspto-grants-1979_01
Patent number
US04134985

Reaction notes

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