Triethylamine → HCID 20393665, compound

HRID 1862810Notes

Reaction equation

HRID 1862810 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16]2[O:20][N:19]=[C:18]([CH3:21])[N:17]=2)=[CH:10][CH:9]=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH3:21][C:18]1[N:17]=[C:16]([N:15]([CH2:14][C:11]2[CH:12]=[CH:13][C:8]([CH3:7])=[CH:9][CH:10]=2)[C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:5])[O:20][N:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 203936303-Methyl-N-[(4-methylphenyl)methyl]-1,2,4-oxadiazol-5-amine

Product 1

HCID 20393665HCID 20393665, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Cyclopropane carboxylic acid chloride (3.45 g, 0.033 mole) was added dropwise to a solution of 5-(4-methylphenyl)methylamino-3-methyl-1,2,4-oxadiazole (6.1 g, 0.03 mole) and triethylamine (3.45 g, 0.035 mole) in dry benzene keeping the temperature below 10° C. After the addition the temperature was allowed to reach room temperature and then refluxed overnight. On cooling the reaction mixture was washed twice with 2 N HCl and twice with a saturated solution of NaHCO3 and dried over MgSO4 and charcoaled. The product was purified by column chromatography--silica gel (110 g) eluting with petroleum ether 40°-60° C. increasing polarity to 10% ether in petroleum ether. The title compound was recrystallised from petroleum ether 60°-80° C. as white needles. m.p. 49.5°-50.5° C.

Workup

  1. additionAfter the addition the temperature
  2. customto reach room temperature
  3. temperaturerefluxed overnight
  4. temperatureOn cooling the reaction mixture
  5. washwas washed twice with 2 N HCl and twice with a saturated solution of NaHCO3
  6. dry with materialdried over MgSO4
  7. customThe product was purified by column chromatography
  8. washsilica gel (110 g) eluting with petroleum ether 40°-60° C.
  9. temperatureincreasing polarity to 10% ether in petroleum ether
  10. customThe title compound was recrystallised from petroleum ether 60°-80° C. as white needles

Sources & evidence

ORD record
ord-311f04f82a664772a5d943986e123245
Source dataset
uspto-grants-1979_09
Patent number
US04166818

Reaction notes

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