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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 67356Generated: October 29, 2026

L-Proline → (S)-6-chloro-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione

https://huagongshe.com/reaction/67356

Reaction equation

Participants

RoleNameHCIDCharge
ReactantL-ProlineHCID 145742—
Reactant5-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneHCID 639058—
SolventDimethyl SulfoxideHCID 679—
Product(S)-6-chloro-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dioneHCID 22819143—

Reaction Steps

10 g (50.6 mmol) of 6-chloroisatoic acid anhydride are stirred at 110° C. for 2 hours with 5.82 g (50.6 mmol) of L-proline in 80 ml of dimethyl sulphoxide. The solution is evaporated and the residue is crystallised from ethyl acetate. There is obtained (S)-6-chloro-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione of melting point 264°-266° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04346031
Source datasetuspto-grants-1982_08
ORD IDord-2a11cb1a14da49629f13228a9b9f9fa0
Source noteuspto-grants-1982_08