Triethylamine → N-ethyl-2-thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxamide

https://huagongshe.com/reaction/2041008

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Ethylamine hydrochloride	HCID 11198	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	2-Sulfanyl-1,3-benzoxazole-6-carboxylic acid	HCID 20734770	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	N-ethyl-2-thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxamide	HCID 86631910	—

Reaction Steps

2-Thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid (Example 92B, 424 mg, 2.17 mmol), ethanamine hydrochloride (266 mg, 3.26 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (991 mg, 2.61 mmol) were combined in tetrahydrofuran (5 mL). Triethylamine (1.4 mL, 977 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane, washed with a 1 N aqueous solution of hydrochloric acid, and absorbed on silica gel. The crude mixture was purified with silica gel chromatography eluting with a gradient of methanol in dichloromethane (2-20%). The chromatographed material was triturated with dichloromethane to afford the title compound. MS (ESI−) m/z 220.9 (M−H)−.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08580968B2
Source dataset	uspto-grants-2013_11
ORD ID	ord-8dcd81a9c3bc49789e8bce884100db86
Source note	uspto-grants-2013_11