N,N-Dimethyl-1,3-propanediamine → 80092-76-8

HRID 1578086Notes

Reaction equation

HRID 1578086 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[CH2:8][CH:9]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=4[Cl:25])[CH2:10][C:11](=O)[C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1.[CH3:26][N:27]([CH3:32])[CH2:28][CH2:29][CH2:30][NH2:31]>C(O)C>[Cl:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[CH2:8][CH:9]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=4[Cl:25])[CH2:10][C:11](=[N:31][CH2:30][CH2:29][CH2:28][N:27]([CH3:32])[CH3:26])[C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 633805HCID 633805, compound

Product 1

HCID 54723180092-76-8

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3.10 g of 7-chloro-3-(2,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione and 1.6 g of N,N-dimethyl-1,3-propanediamine in 125 ml of ethanol is heated under reflux for 1.5 hrs. Approximately 65 ml of solvent is removed by distillation and the resulting turbid solution is filtered. The filtrate is diluted with 50 ml of ether and chilled to 0° C. The solid is collected and recrystallized from a mixture of dichloromethane/ethyl acetate. Dry in vacuo at 80° C. for 4 hrs gives 7-chloro-3-(2,4-dichlorophenyl)-1-[[3-(dimethylamino)propyl]imino]-1,3,4,10-tetrahydro-9(2H)acridinone; mp 168°-170° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1.5 hrs
  3. customApproximately 65 ml of solvent is removed by distillation
  4. filtrationthe resulting turbid solution is filtered
  5. additionThe filtrate is diluted with 50 ml of ether
  6. customThe solid is collected
  7. customrecrystallized from a mixture of dichloromethane/ethyl acetate
  8. customDry in vacuo at 80° C. for 4 hrs

Sources & evidence

ORD record
ord-5708c73a959e4e8280894eea88d530a4
Source dataset
uspto-grants-1981_09
Patent number
US04291034

Reaction notes

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