Potassium Iodide → N'-(4-Diethylaminoacetylaminophenyl)-N,N-Dimethylacetamidine

HRID 461882Notes

Reaction equation

HRID 461882 reaction equation
[I-].[K+].Cl.Cl[CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]=[C:16]([N:18]([CH3:20])[CH3:19])[CH3:17])=[CH:11][CH:10]=1)=[O:7].[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22].C1(S(O)(=O)=O)C(S(O)(=O)=O)=CC=C2C=1C=CC=C2>C(O)C>[CH2:21]([N:23]([CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]=[C:16]([N:18]([CH3:20])[CH3:19])[CH3:17])=[CH:11][CH:10]=1)=[O:7])[CH2:24][CH3:25])[CH3:22]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8021DiethylamineHCID 3015207Naphthalenedisulfonic acidHCID 21392874N'-(4-Chloroacetylaminophenyl)-N,N-dimethylacetamidine hydrochloride

Product 1

HCID 21392890N'-(4-Diethylaminoacetylaminophenyl)-N,N-Dimethylacetamidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 g of potassium iodide is added to a solution of 23.2 g of N'-(4-chloroacetylaminophenyl)-N,N-dimethylacetamidine hydrochloride in 250 ml of ethanol and 14.6 g of diethylamine are added dropwise at 20° C. The mixture is heated under reflux for 2 hours and evaporated in vacuo, the residue is dissolved in water, sodium hydroxide solution is added and the organic phase is extracted with ether/chloroform. After distilling the organic phase, 7.9 g of N'-(4-diethylaminoacetylaminophenyl)-N,N-dimethylacetamidine, boiling point0.2 185°-187° C, are obtained. Addition of 1 mol of naphthalenedisulphonic acid to 1 mol of the base gives the naphthalenedisulphonate, melting point >260° C (decomposition) (recrystallized from ethanol/H2O). The naphthalene-disulphonate is best prepared from the crude undistilled base and naphthalenedisulphonic acid.

Workup

  1. additionare added dropwise at 20° C
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for 2 hours
  4. customevaporated in vacuo
  5. dissolutionthe residue is dissolved in water
  6. additionsodium hydroxide solution is added
  7. extractionthe organic phase is extracted with ether/chloroform
  8. distillationAfter distilling the organic phase, 7.9 g of N'-(4-diethylaminoacetylaminophenyl)-N,N-dimethylacetamidine
  9. customboiling point0.2 185°-187° C
  10. customare obtained
  11. customgives
  12. customthe naphthalenedisulphonate, melting point >260° C (decomposition) (recrystallized from ethanol/H2O)
  13. customThe naphthalene-disulphonate is best prepared from the crude undistilled base and naphthalenedisulphonic acid

Sources & evidence

ORD record
ord-2a643bb6f8d84f74a288952fbb0003be
Source dataset
uspto-grants-1977_12
Patent number
US04064270

Reaction notes

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