Benzoyl chloride → Methyl 2-phenyl-benzoxazole-6-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Benzoyl chloride	HCID 7412	—
Reactant	Benzoic acid, 4-amino-3-hydroxy-, methyl ester	HCID 7020619	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Methyl 2-phenyl-benzoxazole-6-carboxylate	HCID 10586965	85.6%

Reaction Conditions

Temperature	210 °C

Reaction Steps

A mixture of methyl 4-amino-3-hydroxy-benzoate 1s (0.3 g, 1.8 mmol) and benzoyl chloride 1t (0.23 mL, 2.0 mmol) in dioxane (2.5 mL) was heated at 210° C. under microwave for 15 min. The reaction mixture was diluted with CH2Cl2 and washed with aq. NaHCO3. The organic solution was dried over Na2SO4, concentrated and purified by flash column chromatography (silica gel, 20% EtOAc/heptane) to give 1u (0.39 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08697683B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-5da625cebf324701a7105f7aac27bb65
Source note	uspto-grants-2014_04