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

HRID 1446910Notes

Reaction equation

HRID 1446910 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 6 N 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 6 N 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-cb58491186eb4580bfa5540fcf032c0c
Source dataset
uspto-grants-1982_02
Patent number
US04314061

Reaction notes

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