Toluene → HCID 178424354, compound

HRID 1902874Notes

Reaction equation

HRID 1902874 reaction equation
Cl.Cl.[CH2:3]([O:10][NH:11][CH2:12][CH2:13][NH2:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(C)C=CC=CC=1[C:21](Cl)=[NH:22].[OH-].[Na+].[C:27]1([CH3:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.CCOCC>[CH2:3]([O:10][N:11]1[CH2:12][CH2:13][NH:14][C:21]1=[N:22][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH3:33])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 20401292HCID 20401292, compoundHCID 57361558HCID 57361558, compound

Product 1

HCID 178424354HCID 178424354, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 3283Diethyl EtherSolvent

Procedure

A suspension of 21.6 g of N-(benzyloxy)ethylenediamine dihydrochloride in 250 ml of toluene is treated with 18.8 g of o-tolylimidocarbonyl chloride, 3.4 g of tetra-n-butylammonium hydrogen sulfate and, while stirring vigorously, dropwise with 80 ml of 28 percent sodium hydroxide. In so doing, the temperature rises to 52°. The mixture is stirred overnight and diluted with ether. The organic phase is separated, washed with water and extracted three times with 3 N sulfuric acid. The aqueous-acidic phase is made alkaline with concentrated sodium hydroxide and extracted with ether. The ethereal solution is dried and evaporated in vacuo. There is obtained 1-(benzyloxy)-2-[(o-tolyl)imino]imidazolidine as a viscous oil which is used directly in the next step.

Workup

  1. customrises to 52°
  2. customThe organic phase is separated
  3. washwashed with water
  4. extractionextracted three times with 3 N sulfuric acid
  5. extractionextracted with ether
  6. customThe ethereal solution is dried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-04cf1a7fecc94e86a7d42b107466e463
Source dataset
uspto-grants-1982_12
Patent number
US04366160

Reaction notes

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