1,2-Ethanediamine, 4-methylbenzenesulfonate (1:?) → 2-(2,5-DICL PH IMINO)IMIDAZOLIDINE

HRID 1578056Notes

Reaction equation

HRID 1578056 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][C:10](=[N:13][C:14](=O)[CH3:15])SC.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N)C[NH2:30]>CCCCCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][C:10]1[NH:30][CH2:15][CH2:14][N:13]=1

Participants

4

Reactant 2

HCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 178503869HCID 178503869, compound

Product 1

HCID 117777242-(2,5-DICL PH IMINO)IMIDAZOLIDINE

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

2.8 g (0.01 M) of N-(2,5-dichlorophenyl)-N'-acetyl-S-methylisothiourea and 7.0 g (0.03 M) of ethylenediamine mono-p-toluenesulphonate are boiled with 30 ml of n-amyl alcohol for 5 hours. The reaction solution is washed with 50 ml of a saturated solution of sodium carbonate and 50 ml of water. The amyl alcohol is distilled off under vacuum until a dry residue is obtained which after being recrystallized from ethylacetate gives 1.5 g (65% of the theoretical yield of 2-(2',5'-dichlorophenylamino)-imidazoline (2) with a melting point of 179°-182° C. The hydroiodide salt of the above compound has a melting point of 275°-277° C. According to the U.S. Pat. No. 2,899,426 the melting point of 2-(2',5'-dichlorophenylamino)-imidazoline-(2) hydroiodide is 275.4°-277°.

Workup

  1. washThe reaction solution is washed with 50 ml of a saturated solution of sodium carbonate and 50 ml of water
  2. distillationThe amyl alcohol is distilled off under vacuum until a dry residue
  3. customis obtained which
  4. customafter being recrystallized from ethylacetate

Sources & evidence

ORD record
ord-34b7a22e0b664e9396c9f8d77274cafd
Source dataset
uspto-grants-1981_09
Patent number
US04290971

Reaction notes

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