Triethylamine → HCID 20393665, compound

HRID 972074Notes

Reaction equation

HRID 972074 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, 0.03 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 2N HCl and twice with a saturated solution of NaHCO3 and dried over Mg SO4 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 2N HCl and twice with a saturated solution of NaHCO3
  6. dry with materialdried over Mg SO4
  7. customThe product was purified by column chromatography-silica gel (110 g)
  8. washeluting 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-a1ca3e239b0540aaaca4e38a008689c3
Source dataset
uspto-grants-1979_07
Patent number
US04163048

Reaction notes

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