N-Methylethylenediamine → 1-Methyl-2(1,3-dimethyl-5-pyrazolyl) amino-2-imidazoline

HRID 224853Notes

Reaction equation

HRID 224853 reaction equation
I.[CH3:2][N:3]1[C:7]([NH:8][C:9](=N)SC)=[CH:6][C:5]([CH3:13])=[N:4]1.[CH3:14][NH:15][CH2:16][CH2:17][NH2:18]>C(Cl)Cl>[CH3:14][N:15]1[CH2:16][CH2:17][N:18]=[C:9]1[NH:8][C:7]1[N:3]([CH3:2])[N:4]=[C:5]([CH3:13])[CH:6]=1

Participants

4

Reactant 2

HCID 8014N-MethylethylenediamineHCID 178504016HCID 178504016, compound

Product 1

HCID 127638581-Methyl-2(1,3-dimethyl-5-pyrazolyl) amino-2-imidazoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N(1,3-Dimethyl-5-pyrazolyl)-5-methyl isothiourea hydroiodide (Example XXV) (20.0 g) and 11.5 g. N-methyl ethylenediamine were heated to 120° for 30 minutes and to 160° for 1 hour. After cooling, methylene chloride was added and the solid which formed was filtered and discarded. The methylene chloride solution was shaken with 15% KOH solution, dried over potassium carbonate, concentrated and the residue crystallized from acetonitrile to get 10.16 g. product, mp 128°-130°.

Workup

  1. temperatureAfter cooling
  2. customthe solid which formed
  3. filtrationwas filtered
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated
  6. customthe residue crystallized from acetonitrile
  7. customto get 10.16 g

Sources & evidence

ORD record
ord-ac516ea445bf4a238290123fb7b46ed1
Source dataset
uspto-grants-1980_11
Patent number
US04234594

Reaction notes

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