Diethyl Ether → 2-(4-Allyloxy-3,5-dimethyl-phenyl)-5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazole

HRID 1676142Notes

Reaction equation

HRID 1676142 reaction equation
[CH2:1]([C:5]1[C:6]([CH3:28])=[C:7]([C:10]([NH:12][NH:13][C:14](=O)[C:15]2[CH:20]=[C:19]([CH3:21])[C:18]([O:22][CH2:23][CH:24]=[CH2:25])=[C:17]([CH3:26])[CH:16]=2)=[O:11])[S:8][CH:9]=1)[CH:2]([CH3:4])[CH3:3].[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O.C(OCC)C>C1COCC1>[CH2:23]([O:22][C:18]1[C:19]([CH3:21])=[CH:20][C:15]([C:14]2[O:11][C:10]([C:7]3[S:8][CH:9]=[C:5]([CH2:1][CH:2]([CH3:3])[CH3:4])[C:6]=3[CH3:28])=[N:12][N:13]=2)=[CH:16][C:17]=1[CH3:26])[CH:24]=[CH2:25]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 673514084-allyloxy-3,5-dimethyl-benzoic acid N'-(4-isobutyl-3-methyl-thiophene-2-carbonyl)-hydrazide

Product 1

HCID 673506622-(4-Allyloxy-3,5-dimethyl-phenyl)-5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazoleYield 118.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-allyloxy-3,5-dimethyl-benzoic acid N′-(4-isobutyl-3-methyl-thiophene-2-carbonyl)-hydrazide (160 mg, 0.4 mmol) and (methoxycarbonyl-sulfamoyl)triethylammonium hydroxide (350 mg, 1.27 mmol) in dry THF (5 mL) is heated at 110° C. in a microwave oven for 6 min. The mixture is poured into diethyl ether (10 mL) and washed with 1M aq. HCl (10 mL). The aq. phase is re-extracted with ether (10 mL). The combined organic extracts are dried (Na2SO4), filtered and evaporated to give 181 mg of crude 2-(4-allyloxy-3,5-dimethyl-phenyl)-5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazole; LC-MS: tR=1.23 min, [M+1]+=383.35.

Workup

  1. washwashed with 1M aq. HCl (10 mL)
  2. extractionThe aq. phase is re-extracted with ether (10 mL)
  3. dry with materialThe combined organic extracts are dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3b7ad54978de4b2fb19bdc5b1765a146
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

Loading…