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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1425069Generated: November 2, 2026

Thionyl Chloride → Methyl 4-[(7-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate

https://huagongshe.com/reaction/1425069

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThionyl ChlorideHCID 24386—
ReactantMethyl 4-[(7-amino-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoateHCID 28320862—
Reactant4-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 67548929—
SolventPyridineHCID 1049—
ProductMethyl 4-[(7-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoateHCID 6754847370.3%

Reaction Steps

The same operation as in Example (91c) was performed using 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid (0.21 g, 1.2 mmol), thionyl chloride (2 mL), methyl 4-[(7-amino-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate obtained in Example (101b) (0.28 g, 0.97 mmol) and pyridine (5 mL). The resulting solid was washed with dichloromethane/hexane=1/1 to obtain 0.31 g of the title compound as a light yellow solid (70%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08927588B2
Source datasetuspto-grants-2015_01
ORD IDord-45a20ad3c132461e86e4609ce7487205
Source noteuspto-grants-2015_01