p-Toluenesulfonic acid → HCID 20529068, compound

HRID 66763

Reaction equation

HRID 66763 reaction equation
ClC1C=CC=CC=1NCC#N.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([OH:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(N)CN.CC1C=CC(S(O)(=O)=O)=CC=1.[Cl:38][C:39]1[CH:51]=[CH:50][CH:49]=[CH:48][C:40]=1[NH:41][CH2:42][C:43]1[NH:44][CH2:45][CH2:46][N:47]=1>O.ClC1C=CC=CC=1Cl>[C:12]1([CH3:22])[CH:13]=[CH:14][C:15]([S:18]([OH:21])(=[O:19])=[O:20])=[CH:16][CH:17]=1.[Cl:38][C:39]1[CH:51]=[CH:50][CH:49]=[CH:48][C:40]=1[NH:41][CH2:42][C:43]1[NH:47][CH2:46][CH2:45][N:44]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acid2×HCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 12832554HCID 12832554, compoundHCID 13123534HCID 13123534, compound

Product 1

HCID 20529068HCID 20529068, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 72391,2-DichlorobenzeneSolvent

Procedure

The compound 2-((2-chloroanilino)methyl)-2-imidazoline p-toluenesulfonate was prepared using substantially the same procedure described above by heating a mixture of o-chloroanilinoacetonitrile (43.9 g), ethylenediamine p-toluenesulfonate (61.5 g) and 1,2-dichlorobenzene (198 ml). The p-toluenesulfonate salt was hydrolyzed to the free base, i.e., 2-((2-chloroanilino)methyl)-2-imidazoline by slurrying the p-toluenesulfonate salt in water, basifying the slurry and extracting the mixture with CH2Cl2. The methylene chloride was evaporated leaving 38.0 g of the free base. The free base was put in solution in isopropyl alcohol and acidified with hydrochloric acid in isopropyl alcohol which resulted in crystal formation.

Workup

  1. temperatureby heating
  2. extractionextracting the mixture with CH2Cl2
  3. customThe methylene chloride was evaporated

Sources & evidence

ORD record
ord-ff23076f9cdd42e0951ae0a9c3896e80
Source dataset
uspto-grants-1982_08
Patent number
US04343810

Linked notes

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