3,4-Diethoxybenzoic acid → 5-(3,4-Diethoxyphenyl)-3-(2-methylbenzofuran-5-yl)-1,2,4-oxadiazole

HRID 2046108Notes

Reaction equation

HRID 2046108 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([CH3:13])=[CH:10][C:9]=2[CH:14]=1)=[NH:4].[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[O:27][CH2:28][CH3:29])[C:21](O)=O)[CH3:16].ONC(=N)C1C=CC(OC(C)C)=C(I)C=1.ClC1C=C(C=CC=1OCCC)C(O)=O>>[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([C:21]2[O:1][N:2]=[C:3]([C:5]3[CH:6]=[CH:7][C:8]4[O:12][C:11]([CH3:13])=[CH:10][C:9]=4[CH:14]=3)[N:4]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH2:28][CH3:29])[CH3:16]

Participants

5

Reactant 4

HCID 794173,4-Diethoxybenzoic acidHCID 87071503-Chloro-4-propoxybenzoic acidHCID 178422061HCID 178422061, compound2×HCID 178458442HCID 178458442, compound

Product 1

HCID 461999945-(3,4-Diethoxyphenyl)-3-(2-methylbenzofuran-5-yl)-1,2,4-oxadiazoleYield 6%

Procedure

The product Step A was converted to N-hydroxy-2-methylbenzofuran-5-carboximidamide by method described for Example 36, Step A. When N-hydroxy-2-methylbenzofuran-5-carboximidamide and 3,4-diethoxybenzoic acid were substituted for N-hydroxy-3-iodo-4-isopropoxybenzimidamide and 3-chloro-4-propoxybenzoic acid, respectively, in Example 36, Step B, the similar procedure afforded the title compound in 6% yield, as colourless solid. 1H-NMR (CDCl3) 8.28 (bs, 1H); 8.00 (dd, 1H, J=8.55, 1.68 Hz); 7.8 (dd, 1H, J=8.4, 1.98 Hz); 7.68 (d, 1H, J=1.92 Hz); 7.47 (d, 1H, J=8.58 Hz); 6.97 (d, 1H, J=8.46 Hz); 6.45 (s, 1H); 4.23-4.16 (m, 4H); 2.48 (3H); 1.52-1.47 (m, 6H).

Sources & evidence

ORD record
ord-4b884da8b69843e6bda153ed0ef2b79d
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

Loading…