Triethylamine → HCID 178486081, compound

HRID 620400Notes

Reaction equation

HRID 620400 reaction equation
C([N:3](CC)CC)C.Cl.N=[C:10]1[CH:15]=[CH:14][N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]=[CH:11]1.[CH3:22][N:23]=[C:24]=[S:25]>CC(C)=O>[CH3:22][NH:23][C:24]([CH:10]1[CH:15]=[CH:14][N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:12][C:11]1=[NH:3])=[S:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11167Methyl isothiocyanateHCID 21246174HCID 21246174, compound

Product 1

HCID 178486081HCID 178486081, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

5.3 g (52.4 millimoles) of triethylamine were added dropwise to 10.0 g (48.2 millimoles) of 1,4-dihydro-4-imino-1-phenylpyridazine hydrochloride in 25 ml (26.7 g, 365 millimoles) of methyl isothiocyanate at room temperature, while stirring. After the addition was complete, the reaction mixture was diluted with 50 ml of acetone and stirred for a further 2 hours at room temperature. The product was filtered off under suction, washed with water and acetone and recrystallized from dimethylformamide/water. The crystals obtained were suspended in 25 ml of acetone, filtered off under suction, again suspended in 25 ml of acetone and filtered off under suction, and the product was recrystallized from isopropanol. 2.8 g (24% of theory) of 1,4-dihydro-4-(methylthiocarbamyl)-imino-1-phenylpyridazine were isolated as yellow crystals of melting point 177°-178° C. (decomposition).

Workup

  1. additionAfter the addition
  2. stirringstirred for a further 2 hours at room temperature
  3. filtrationThe product was filtered off under suction
  4. washwashed with water and acetone
  5. customrecrystallized from dimethylformamide/water
  6. customThe crystals obtained
  7. filtrationfiltered off under suction
  8. filtrationfiltered off under suction
  9. customthe product was recrystallized from isopropanol

Sources & evidence

ORD record
ord-f8e6f26a916648279077b65184966691
Source dataset
uspto-grants-1989_04
Patent number
US04820821

Reaction notes

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