Water → 5-(3-Chloro-thiophen-2-yl)-3-(4-trifluoromethoxy-phenyl)-[1,2,4]oxadiazole

HRID 2114913

Reaction equation

HRID 2114913 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](Cl)=[O:8].[F:10][C:11]([F:24])([F:23])[O:12][C:13]1[CH:22]=[CH:21][C:16]([C:17](=[N:19]O)[NH2:18])=[CH:15][CH:14]=1.N1C=CC=CC=1.O>O1CCOCC1>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[O:8][N:19]=[C:17]([C:16]2[CH:15]=[CH:14][C:13]([O:12][C:11]([F:10])([F:23])[F:24])=[CH:22][CH:21]=2)[N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 27333094-(Trifluoromethoxy)benzamidoximeHCID 27358243-Chlorothiophene-2-carbonyl chloride

Product 1

HCID 101323925-(3-Chloro-thiophen-2-yl)-3-(4-trifluoromethoxy-phenyl)-[1,2,4]oxadiazoleYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-chloro-thiophene-2-carbonyl chloride (72.4 mg, 0.4 mmol) and 4-trifluoromethoxybenzamidoxime (88 mg, 0.4 mmol) in dioxane:pyridine (11 mL, 10:1) was refluxed for 10 h and cooled to room temperature. To the stirred solution was added 20 mL of water to produce precipitates. The solid was collected by filtration and washed with dioxane:water (1:3), and dried to yield 103 mg (75%) of the title compound.

Workup

  1. customto produce
  2. customprecipitates
  3. filtrationThe solid was collected by filtration
  4. washwashed with dioxane:water (1:3)
  5. customdried

Sources & evidence

ORD record
ord-5526b1a6d095463c83966224161e3a1f
Source dataset
uspto-grants-2008_10
Patent number
US07435750B2

Linked notes

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