Sodium hydride → 3,6-Bis(4-chlorobutoxy)acridine hydrochloride

HRID 1446921Notes

Reaction equation

HRID 1446921 reaction equation
[H-].[Na+].[CH:3]1[C:16]2[C:7](=[N:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[C:11]([OH:17])[CH:10]=3)[CH:6]=[C:5]([OH:18])[CH:4]=1.[Cl:19][CH2:20][CH2:21][CH2:22][CH2:23]OS(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[ClH:19].[Cl:19][CH2:20][CH2:21][CH2:22][CH2:23][O:18][C:5]1[CH:4]=[CH:3][C:16]2[C:7]([CH:6]=1)=[N:8][C:9]1[C:14](=[CH:13][CH:12]=[C:11]([O:17][CH2:23][CH2:22][CH2:21][CH2:20][Cl:19])[CH:10]=1)[CH:15]=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 124221284-Chlorobutyl 4-methylbenzenesulfonateHCID 135482596Acridine-3,6-diol

Product 1

HCID 205534713,6-Bis(4-chlorobutoxy)acridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 11.8 g. of sodium hydride (61.1% dispersion in oil) and 26.0 g. of 3,6-acridinediol is added 250 ml. of dimethylformamide. The mixture is stirred at room temperature for 1.5 hours, then 52.5 g. of 4-chlorobutyl-p-toluenesulfonate are added. This mixture is stirred at room temperature for 3 hours and 20 minutes and then at 50° C. for 2 hours. The volatile materials are removed under reduced pressure at 35°-40° C. The residue is quenched with 1200 ml. of ice-cold saturated aqueous sodium bicarbonate. The resulting tan crystals are collected and dissolved in 500 ml. of chloroform, 30 ml. of 6 N hydrochloric acid in isopropanol are added and the mixture is diluted with ether, giving the desired product as the hydrochloride salt.

Workup

  1. additionTo a mixture of 11.8 g
  2. stirringThis mixture is stirred at room temperature for 3 hours and 20 minutes
  3. waitat 50° C. for 2 hours
  4. customThe volatile materials are removed under reduced pressure at 35°-40° C
  5. customThe residue is quenched with 1200 ml
  6. customThe resulting tan crystals are collected
  7. dissolutiondissolved in 500 ml
  8. additionof 6 N hydrochloric acid in isopropanol are added
  9. additionthe mixture is diluted with ether

Sources & evidence

ORD record
ord-dd578601a4e14a4aa06a5b133593bd49
Source dataset
uspto-grants-1982_02
Patent number
US04314061

Reaction notes

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