Sodium hydride → 3,6-Bis(3-chloropropoxy)acridine--hydrogen chloride (1/1)

HRID 2309686Notes

Reaction equation

HRID 2309686 reaction equation
[H-].[Na+].S([O:7][C:8]1[CH:9]=[CH:10][C:11]2[C:20]([CH:21]=1)=[N:19][C:18]1[C:13](=[CH:14][CH:15]=[C:16]([OH:22])[CH:17]=1)[CH:12]=2)(O)(=O)=O.[Cl:23][CH2:24][CH2:25][CH2:26]OS(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[ClH:23].[Cl:23][CH2:24][CH2:25][CH2:26][O:7][C:8]1[CH:9]=[CH:10][C:11]2[C:20]([CH:21]=1)=[N:19][C:18]1[C:13](=[CH:14][CH:15]=[C:16]([O:22][CH2:26][CH2:25][CH2:24][Cl:23])[CH:17]=1)[CH:12]=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 694343-Chloropropyl p-toluenesulfonateHCID 137195957HCID 137195957, compound

Product 1

HCID 201846633,6-Bis(3-chloropropoxy)acridine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 11.80 g. of sodium hydride (61.14% oil dispersion) and 26.0 g. of 3,6-acridinediol sulfate (2:1) is added 250 ml. of dry N,N-dimethylformamide. The mixture is stirred at room temperature for 1.5 hours, then 49.8 g. of 3-chloropropyl-p-toluene sulfonate are added. This mixture is stirred at room temperature for 3 hours and 20 minutes, then at 50° C. for 2 hours. The volatile materials are removed under reduced pressure at 35°-40° C. and the residue is quenched with 1200 ml. of ice-cold saturated aqueous sodium bicarbonate solution. The resulting tan crystals are collected and dissolved in 500 ml. of chloroform. A 30 ml. portion of 6N hydrochloric acid in isopropanol is added and the mixture is diluted with ether. The solid is collected and recrystallized from ether, giving the desired product as tan crystals, m.p. 211°-213° C.

Workup

  1. additionTo a mixture of 11.80 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. additionportion of 6N hydrochloric acid in isopropanol is added
  9. additionthe mixture is diluted with ether
  10. customThe solid is collected
  11. customrecrystallized from ether

Sources & evidence

ORD record
ord-02adb90c7d3f4611aac160147200240d
Source dataset
uspto-grants-1987_09
Patent number
US04696935

Reaction notes

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