2-AMINO-5-(4-CHLOROPHENYL)-1 3 4-OXADIA& synthesis

12synthesis methods

Product Name:2-AMINO-5-(4-CHLOROPHENYL)-1 3 4-OXADIA&
CAS Number:33621-61-3
Molecular formula:C8H6ClN3O
Molecular Weight:195.61

563-41-7
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104-88-1 Synthesis

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2-AMINO-5-(4-CHLOROPHENYL)-1 3 4-OXADIA&

33621-61-3
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$48.00/1g

Yield:33621-61-3 61%

Reaction Conditions:

Stage #1: hydrazinecarboxamide monohydrochloride;4-chlorobenzaldehydewith anhydrous Sodium acetate in tetrahydrofuran;lithium hydroxide monohydrate; for 1.5 h;Cooling with ice;
Stage #2: with chloramine-T;potassium carbonate in tetrahydrofuran;lithium hydroxide monohydrate at 20; for 3 h;

Steps:

C12 Example C12

Example C12
Production of 5-(4-chlorophenyl)-1,3,4-oxadiazol-2-amine
A solution of semicarbazide hydrochloride (1.22 g, 10.9 mmol) and sodium acetate (0.897 g, 10.9 mmol) in water (10 mL) was cooled in ice, then 4-chlorobenzaldehyde (1.46 g, 10.4 mmol) and tetrahydrofuran (THF) (3.0 mL) were added thereto, and the mixture was stirred. 1.5 hours later, tetrahydrofuran (THF) (27 mL), potassium carbonate (3.60 g, 26.0 mmol), and chloramine T trihydrate (4.84 g, 17.2 mmol) were added to the reaction solution, and the mixture was stirred at room temperature. 3 hours later, the reaction solution was washed with a 2:1 mixed solution of a 20% sodium bisulfite aqueous solution and 30% aqueous sodium chloride solution. 4 mol/L hydrochloric acid in ethyl acetate (7.8 mL, 31.2 mol) was added to the obtained organic layer, and the mixture was stirred at room temperature. 30 minutes later, the resulting solid was collected by filtration and washed with tetrahydrofuran (THF).
Toluene was added to the filtrate, followed by extraction with a 4:1 mixed solution of 2 mol/L hydrochloric acid and 30% aqueous sodium chloride solution.
The solid collected by filtration earlier was added to the obtained aqueous layer, and the mixture was further adjusted to pH 12 or higher by the addition of a 10 mol/L sodium hydroxide aqueous solution.
After overnight stirring, the solid was collected by filtration, washed with water, and then dried under reduced pressure to obtain the title compound (1.25 g, yield: 61%) as a white solid.
¹H-NMR (400 MHz, DMSO-D₆) δ: 7.81-7.78 (2H, m), 7.62-7.59 (2H, m), 7.31 (2H, brs)
ESI-MS (m/z): 196, 198 (M+H)⁺

References:

US2022/169640,2022,A1 Location in patent:Paragraph 0293-0295