4-Propylbenzoic acid → 3-(2-Chloro-5-iodo-4-isopropoxyphenyl)-5-(4-propylphenyl)-1,2,4-oxadiazole

HRID 2046118Notes

Reaction equation

HRID 2046118 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]([CH3:15])[CH3:14])[C:9]([I:16])=[CH:8][C:3]=1[C:4](=[NH:7])[NH:5][OH:6].[CH2:17]([C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=O)=[CH:22][CH:21]=1)[CH2:18][CH3:19].ONC(=N)C1C=CC(OC(C)C)=C(I)C=1.ClC1C=C(C=CC=1OCCC)C(O)=O>>[Cl:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]([CH3:14])[CH3:15])[C:9]([I:16])=[CH:8][C:3]=1[C:4]1[N:7]=[C:24]([C:23]2[CH:27]=[CH:28][C:20]([CH2:17][CH2:18][CH3:19])=[CH:21][CH:22]=2)[O:6][N:5]=1

Participants

5

Reactant 4

HCID 1376014-Propylbenzoic acidHCID 87071503-Chloro-4-propoxybenzoic acidHCID 178458442HCID 178458442, compoundHCID 178458487HCID 178458487, compound

Product 1

HCID 666149563-(2-Chloro-5-iodo-4-isopropoxyphenyl)-5-(4-propylphenyl)-1,2,4-oxadiazoleYield 20%

Procedure

When the product of Step A and 4-propylbenzoic acid were substituted for N-hydroxy-3-iodo-4-isopropoxybenzimidamide and 3-chloro-4-propoxybenzoic acid in Example 36, Step B, the similar procedure afforded the title compound in 20% yield, as white solid. 1H NMR (CDCl3) 8.46 (s, 1H); 8.10 (d, 2H, J=8.25 Hz); 7.34 (d, 2H, J=8.28 Hz); 6.92 (s, 1H); 7.67-7.59 (m, 1H); 2.67 (t, 2H, J=7.35 Hz); 1.72-1.65 (m, 2H); 1.43 (d, 6H, J=6.06 Hz); 0.96 (t, 3H, J=7.32 Hz).

Sources & evidence

ORD record
ord-27c051e5404343458fc866df84a7f4c4
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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