Methyl N-(triethylammoniosulfonyl)carbamate → 2-(4-Allyloxy-3,5-dimethyl-phenyl)-5-(5-isobutyl-thiophen-2-yl)-[1,3,4]oxadiazole

HRID 1094305Notes

Reaction equation

HRID 1094305 reaction equation
[CH2:1]([C:5]1[S:9][C:8]([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])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1.C(OCC)C>[CH2:23]([O:22][C:18]1[C:19]([CH3:21])=[CH:20][C:15]([C:14]2[O:11][C:10]([C:8]3[S:9][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][CH:7]=3)=[N:12][N:13]=2)=[CH:16][C:17]=1[CH3:26])[CH:24]=[CH2:25]

Participants

5

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 666369514-allyloxy-3,5-dimethyl-benzoic acid N'-(5-isobutyl-thiophene-2-carbonyl)-hydrazide

Product 1

HCID 666366842-(4-Allyloxy-3,5-dimethyl-phenyl)-5-(5-isobutyl-thiophen-2-yl)-[1,3,4]oxadiazoleYield 76.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-allyloxy-3,5-dimethyl-benzoic acid N′-(5-isobutyl-thiophene-2-carbonyl)-hydrazide (1.40 g, 3.62 mmol) and Burgess reagent (1.12 g, 4.71 mmol) in THF (15 mL) is stirred at 110° C. for 3 min under microwave irradiation. The mixture is diluted with diethyl ether, washed with water, dried over MgSO4, filtered and evaporated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 2-(4-allyloxy-3,5-dimethyl-phenyl)-5-(5-isobutyl-thiophen-2-yl)-[1,3,4]oxadiazole (1.02 g) as a colourless oil; LC-MS: tR=1.21 min, [M+1]+=369.15.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

Sources & evidence

ORD record
ord-b218d54b9c5b46d388165d8399ab5f4f
Source dataset
uspto-grants-2012_03
Patent number
US08133910B2

Reaction notes

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