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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1265919Generated: November 2, 2026

Thionyl Chloride → 8-Chloro-4-[3-(4-chloromethyl-thiazol-2-yl)-phenyl]-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-one

https://huagongshe.com/reaction/1265919

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThionyl ChlorideHCID 24386—
Reactant8-Chloro-7-dimethylamino-4-[3-(4-hydroxymethyl-thiazol-2-yl)-phenyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-oneHCID 18613361—
SolventDichloromethaneHCID 6344—
Product8-Chloro-4-[3-(4-chloromethyl-thiazol-2-yl)-phenyl]-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-oneHCID 18613213—

Reaction Conditions

Temperature40 °C

Reaction Steps

A mixture of 8-chloro-7-dimethylamino-4-[3-(4-hydroxymethyl-thiazol-2-yl)-phenyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-one (0.38 g) (Example 19) and thionyl chloride (0.1 mL) in CH2Cl2 was heated to 40° C. for 2 h. The heterogeneous mixture was evaporated in vacuum and the residue was triturated with AcOEt to give the title compound (0.44 g) as a light-brown solid, MS (ISP) 445.1 [(M+H)+].

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06544985B2
Source datasetuspto-grants-2003_04
ORD IDord-f61b9fcf60604afba56630d10a37a03e
Source noteuspto-grants-2003_04