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

https://huagongshe.com/reaction/1692032

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	US08153813B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-3d9791f29cce4c49910e4e9805392d8c
Source note	uspto-grants-2012_04