Butylamine → N-Butyl-3-methyl-1,2,4-oxadiazol-5-amine

Reaction equation

[CH3:1][C:2]1[N:6]=[C:5](C(Cl)(Cl)Cl)[O:4][N:3]=1.[CH2:11]([NH2:15])[CH2:12][CH2:13][CH3:14]>>[CH2:11]([NH:15][C:5]1[O:4][N:3]=[C:2]([CH3:1])[N:6]=1)[CH2:12][CH2:13][CH3:14]

Participants

Reactant 2

HCID 8007Butylamine

HCID 709533-Methyl-5-(trichloromethyl)-1,2,4-oxadiazole

Product 1

HCID 20393636N-Butyl-3-methyl-1,2,4-oxadiazol-5-amine

Procedure

3-Methyl-5-trichloromethyl-1,2,4-oxadiazole (43 g, 0.21 mole) was added to n-butylamine (46.75 g, 0.63 mole) and stirred at room temperature overnight. Excess amine was removed under vacuum and the residue distilled (oil bath 110° C./0.5 mm Hg). Recrystallisation fromm petroleum ether 60°-80° C. gave the title compound as white plates 26 g, m.p. 62°-65° C.

Workup

customExcess amine was removed under vacuum
distillationthe residue distilled (oil bath 110° C./0.5 mm Hg)
customRecrystallisation fromm petroleum ether 60°-80° C.

Sources & evidence

ORD record: ord-1f11e51b8ea349ccade8b35962502bb4
Source dataset: uspto-grants-1979_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04163048

Reaction notes

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