ChemicalBook CAS DataBase List BENTRANIL

BENTRANIL synthesis

14synthesis methods

Product Name:BENTRANIL
CAS Number:1022-46-4
Molecular formula:C14H9NO2
Molecular Weight:223.23

Bentranil was manufactured as a specialty benzothiazole fungicide, and its commercial production followed the fine chemical synthesis routes typical of mid 20th century protective fungicides. Industrial manufacture began with preparation of the benzothiazole core, followed by controlled acylation and nitrile forming steps to introduce the characteristic substituents that give bentranil its fungicidal activity. These reactions were carried out in batch reactors under anhydrous, temperature regulated conditions, after which the crude product was purified, usually by solvent crystallisation, to yield technical grade bentranil.

88-67-5 Synthesis

88-67-5
570 suppliers
$5.00/5g

100-47-0
382 suppliers
$14.14/25gm:

1022-46-4
81 suppliers
$90.00/25mg

Yield: 87%

Reaction Conditions:

with 1-butyl-3-methylimidazolium hydroxide in neat (no solvent) for 3 h;Green chemistry;Reagent/catalyst;Solvent;Temperature;

Steps:

4H-benzo[d][1,3-]oxazin-4-one: Procedure
General procedure: A mixture of benzonitrile(2.0 mmol) and o-iodobenzoic acid (2.0 mmol) and [bmIm]OH (35mol) was stirred at room temperature for (3-5) h. After completion of reaction as indicated byTLC, 20mL of water was added to the reaction mixture and stirred well. The product was extracted with ether (3×20 mL). The combined organic layers were dried over anhydrous Na₂SO₄ to afford the crude product, this crude product was taken to column in order to obtain analytically pure compound 4(a-m)(77-91%). After isolation of the product, the remaining aqueous layer containing the ionic liquid was washed with ether (2x10mL) to remove organic impurity and filtered. The filtrate was extracted with dichloromethane(2×10mL), dried over MgSO₄ and evaporated under reduced pressure to afford [bmIm]OH, which was reused five times in subsequent runs without further purification.

References:

Waseem, Malik Abdul;Shireen;Srivastava, Anjali;Srivastava, Arjita;Rahila;Siddiqui [Tetrahedron Letters,2014,vol. 55,# 44,p. 6072 - 6076] Location in patent:supporting information

948-65-2 Synthesis