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

HRID 1681923Notes

Reaction equation

HRID 1681923 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:17])[C:10]=1[O:11][CH2:12][CH2:13][CH2:14][C:15]#[CH:16])[C:5]([NH2:7])=[O:6].CO[C:20](OC)([N:22](C)C)[CH3:21].Cl.NO>>[CH3:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][N:22]=[C:20]([CH3:21])[N:7]=2)[CH:8]=[C:9]([CH3:17])[C:10]=1[O:11][CH2:12][CH2:13][CH2:14][C:15]#[CH:16]

Participants

4

Reactant 3

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 443297Hydroxyamine hydrochlorideHCID 150572923,5-Dimethyl-4-(3-ethynylpropoxy)benzamide

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-ethynylpropoxy)benzamide, 31 ml dimethylacetamide dimethyl acetal and 1.7 g hydroxylamine hydrochloride according to the procedure of Example 2, 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-3447ab6062c74549a80e331e4fe6a024
Source dataset
uspto-grants-1992_12
Patent number
US05175178

Reaction notes

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