5-amino-2,3-dihydro-1,3-benzoxazol-2-one

• CAS: 14733-77-8
• Catalog Number: ACM14733778
• Category: Main Products
• Molecular Weight: 150.1
• Molecular Formula: C7H6N2O2
• Appearance: Powder

Case Study

5-Amino-1,3-Benzoxazol-2(3H)-One for the Synthesis of Biphenyl-4-Carboxamide Derivatives

Oka, Hiromasa, et al. Bioorganic & Medicinal Chemistry, 2018, 26(12), 3716-3726.

In order to prepare biphenyl-4-carboxamide derivatives, Suzuki-Miyaura coupling of compound 9 to phenylboronic acid gave the compound 10, which was transformed into benzyl bromide 11. Further nucleophilic substitution of the bromo group with various secondary amines gave us compounds 12a-g. These intermediates were hydrolyzed to give the carboxylic acid derivatives 13a-g. This work had made the desired biphenyl-4-carboxamide derivatives 7, 8, and 14-36 by condensation of 13a-g with anilines containing substituted atoms or fusion with five-, six-, or seven-membered rings.
Synthesis of compound 19 with 5-amino-1,3-benzoxazol-2(3H)-one
· A suspension of compound 13a (500 mg, 1.41 mmol) in 1.5 equivalents of sodium chloride was diluted in 20 mL of DCE. To this mixture, 5-amino-1,3-benzoxazol-2(3H)-one (1.41 mmol) dissolved in 2 mL of DCE was added. The mixture was cooled in an ice-water bath.
· Then added HBTU (694 mg, 1.83 mmol) and N-methylmorpholine (194 mg, 1.92 mmol) and stirred for 30 hours at room temperature.
· After that, the reaction mixture was dissolved in water, and the organic part was removed with chloroform. It was dry organic layer was treated with MgSO4 and solvent evaporated. This residue was then chromatographed using column chromatography on silica gel using CHCl3, MeOH, and 28% water ammonia to get N-(2-oxo-2,3-dihydro-1,3-benzoxazol-5-yl)-2-(piperidin-1-ylmethyl)biphenyl-4-carboxamide.
· The chemical was dissolving in 3 mL of EtOAc, and 1 mL of a 4 M solution of hydrogen chloride in EtOAc. The solvent was evaporated, and the product triturated in ethanol to give compound 19 as white needles, with 50% yield.

Custom Q&A

What is the molecular formula of 5-amino-2,3-dihydro-1,3-benzoxazol-2-one?

The molecular formula is C7H6N2O2.

What is the molecular weight of 5-amino-2,3-dihydro-1,3-benzoxazol-2-one?

The molecular weight is 150.13 g/mol.

What are the synonyms of 5-amino-2,3-dihydro-1,3-benzoxazol-2-one?

The synonyms include 14733-77-8, 5-Aminobenzo[d]oxazol-2(3H)-one, 2(3H)-Benzoxazolone, 5-amino-, 5-amino-1,3-benzoxazol-2(3H)-one, and 5-amino-3H-1,3-benzoxazol-2-one.

What is the IUPAC name of 5-amino-2,3-dihydro-1,3-benzoxazol-2-one?

The IUPAC name is 5-amino-3H-1,3-benzoxazol-2-one.

What is the InChI of 5-amino-2,3-dihydro-1,3-benzoxazol-2-one?

The InChI is InChI=1S/C7H6N2O2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,8H2,(H,9,10).

What is the InChIKey of 5-amino-2,3-dihydro-1,3-benzoxazol-2-one?

The InChIKey is GJXXUHGUCBUXSL-UHFFFAOYSA-N.

What is the canonical SMILES of 5-amino-2,3-dihydro-1,3-benzoxazol-2-one?

The canonical SMILES is C1=CC2=C(C=C1N)NC(=O)O2.

What is the CAS number of 5-amino-2,3-dihydro-1,3-benzoxazol-2-one?

The CAS number is 14733-77-8.

What is the XLogP3 value of 5-amino-2,3-dihydro-1,3-benzoxazol-2-one?

The XLogP3 value is 0.5.

How many hydrogen bond acceptors does 5-amino-2,3-dihydro-1,3-benzoxazol-2-one have?

It has 3 hydrogen bond acceptors.

Synthetic Use

Upstream Synthesis Route 1

• 3889-13-2

• 14733-77-8

Reference: [1]Patent: WO2012/59932,2012,A1 .Location in patent: Page/Page column 165

Downstream Synthesis Route 1

• 14733-77-8

• 14733-73-4

Reference: [1] Journal of Medicinal Chemistry, 1967, vol. 10, p. 408 - 410

Downstream Synthesis Route 2

• 590-28-3
• 14733-77-8

• 101421-11-8

Reference: [1]Journal of the American Chemical Society,1958,vol. 80,p. 1662

Downstream Synthesis Route 3

• 14733-77-8
• 108-24-7

• 103858-71-5

Reference: [1]Chemische Berichte,1960,vol. 93,p. 1331 - 1339

* For details of the synthesis route, please refer to the original source to ensure accuracy.