1,1-Dimethoxyethyl(dimethyl)amine → 5-[3,5-Dimethyl-4-(3-ethynylpropoxy)phenyl]-3-methyl-1,2,4-oxadiazole

HRID 2165914Notes

Reaction equation

HRID 2165914 reaction equation
CO[C:3](OC)([N:5](C)C)[CH3:4].Cl.[NH2:11]O.[CH3:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([CH3:29])[C:22]=1[O:23][CH2:24][CH2:25][CH2:26][C:27]#[CH:28])[C:17]([OH:19])=O>>[CH3:29][C:21]1[CH:20]=[C:16]([C:17]2[O:19][N:5]=[C:3]([CH3:4])[N:11]=2)[CH:15]=[C:14]([CH3:13])[C:22]=1[O:23][CH2:24][CH2:25][CH2:26][C:27]#[CH:28]

Participants

4

Reactant 3

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 443297Hydroxyamine hydrochlorideHCID 150572913,5-Dimethyl-4-(3-ethynylpropoxy)benzoic acid

Product 1

HCID 150572935-[3,5-Dimethyl-4-(3-ethynylpropoxy)phenyl]-3-methyl-1,2,4-oxadiazole

Procedure

5-[3,5-Dimethyl-4-(3-ethynylpropoxy)phenyl]-3-methyl-1,2,4-oxadiazole [XIV; Y=(CH2)3, R1 and R2 =3,5-(CH3)2, R8 =CH3 ] was prepared from 4.7 g 3,5-dimethyl-4-(3-ethylnylpropoxy)benzamide, 31 ml dimethylacetamide dimethyl acetal and 1.7 g hydroxylamine hydrochlorde according to the procedure of Example 1, part (b), and was obtained (4.4 g) in the form of a viscous oil used directly in the next reaction. A sample when crystallized from isopropyl acetate/hexane had the m.p. 38°-40° C.

Workup

  1. customwas obtained (4.4 g) in the form of a viscous oil
  2. customused directly in the next reaction
  3. customA sample when crystallized from isopropyl acetate/hexane

Sources & evidence

ORD record
ord-0a9cd63716aa4667a6ceb7f1018f5687
Source dataset
uspto-grants-1990_07
Patent number
US04942241

Reaction notes

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