Oxalyl chloride → HCID 20158336, compound

HRID 986256Notes

Reaction equation

HRID 986256 reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[CH2:4][CH2:5][N:6]1[C:19]2C(=[CH:15][CH:16]=[CH:17][CH:18]=2)C(=O)[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]1=2)[CH3:2].[C:23]([Cl:28])(=O)[C:24]([Cl:26])=O>ClCCl>[Cl-:26].[Cl:28][C:23]1[C:24]2[C:19]([N+:6]([CH2:5][CH2:4][N:3]([CH2:21][CH3:22])[CH2:1][CH3:2])=[C:7]3[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]3)=[CH:18][CH:17]=[CH:16][CH:15]=2

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 1488839(10H)-Acridinone, 10-(2-(diethylamino)ethyl)-

Product 1

HCID 20158336HCID 20158336, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4.94 g of 10-[2-(diethylamino)ethyl]-9-acridanone, 300 ml of dichloromethane and 2.85 ml (33.6 mmol) of oxalyl chloride is stirred for 20 minutes, the crystals (9-chloro-10-[2-(diethylamino)ethyl]-acridinium chloride) obtained are filtered with ether. This material is taken up in 100 ml of methanol, treated with 2.8 g of N-methyl-N-(2-thiazolyl)hydrazine hydrochloride and 4.1 g of sodium acetate, heated to boiling under reflux for 15 minutes and evaporated. The residue is made alkaline with sodium carbonate solution, extracted with dichloromethane, the extract is washed with water, dried and evaporated. By crystallization of the residue from isopropyl ether there is obtained 10-[2-(diethylamino)ethyl]-9-acridanone methyl(2-thiazolyl)hydrazone of melting point 103°-104°.

Sources & evidence

ORD record
ord-2195fe07fbec498b8ea096fe65110168
Source dataset
uspto-grants-1987_12
Patent number
US04711889

Reaction notes

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