Formaldehyde → 3,6-Bis[2-(diethylamino)ethoxy]-4,5-acridinedimethanol

HRID 979105

Reaction equation

HRID 979105 reaction equation
Cl.Cl.Cl.[CH2:4]([N:6]([CH2:32][CH3:33])[CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[C:22]([CH:23]=1)=[N:21][C:20]1[C:15](=[CH:16][CH:17]=[C:18]([O:24][CH2:25][CH2:26][N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH:19]=1)[CH:14]=2)[CH3:5].[CH2:34]=[O:35].CC[O:38][CH2:39]C>S(=O)(=O)(O)O>[CH2:28]([N:27]([CH2:30][CH3:31])[CH2:26][CH2:25][O:24][C:18]1[CH:17]=[CH:16][C:15]2[C:20]([C:19]=1[CH2:34][OH:35])=[N:21][C:22]1[C:23]([CH2:39][OH:38])=[C:10]([O:9][CH2:8][CH2:7][N:6]([CH2:4][CH3:5])[CH2:32][CH3:33])[CH:11]=[CH:12][C:13]=1[CH:14]=2)[CH3:29]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 3283Diethyl EtherHCID 1625402-[6-[2-(diethylamino)ethoxy]acridin-3-yl]oxy-N,N-diethylethanamine;trihydrochloride

Product 1

HCID 201846723,6-Bis[2-(diethylamino)ethoxy]-4,5-acridinedimethanol

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 23.43 g of 3,6-bis(2-diethylaminoethoxy)acridine trihydrochloride (U.S. Pat. No. 3,740,403) in 85 ml of concentrated sulfuric acid was added 2.94 g of paraformaldehyde. The mixture was stirred 45 minutes, then added to 1.5 liters of ether. The resulting solid was collected, dissolved in water, sodium bicarbonate was added and the mixture extracted with six 75 ml portions of chloroform. These extracts were placed on an alumina column which was then eluted with ether and then methylene chloride. The methylene chloride extract was concentrated, giving 4.0 g of the desired product as yellow crystals, mp 95°-96° C.

Workup

  1. customThe resulting solid was collected
  2. dissolutiondissolved in water
  3. additionsodium bicarbonate was added
  4. extractionthe mixture extracted with six 75 ml portions of chloroform
  5. washwas then eluted with ether
  6. extractionThe methylene chloride extract
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-af187549508f40ed897839d2246f24e4
Source dataset
uspto-grants-1987_05
Patent number
US04666917

Linked notes

Loading…