Triethylamine → HCID 178465505, compound

HRID 620401Notes

Reaction equation

HRID 620401 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.[CH2:22]([N:24]=[C:25]=[S:26])[CH3:23]>CC(C)=O>[CH2:22]([NH:24][C:25]([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:26])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10966Ethyl isothiocyanateHCID 21246174HCID 21246174, compound

Product 1

HCID 178465505HCID 178465505, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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 (24.9 g, 285 millimoles) of ethyl isothiocyanate at room temperature, while stirring. After the addition was complete, the reaction mixture was diluted with 50 ml of acetone, stirred for a further 2 hours at room temperature and then filtered. The residue was discarded. The filtrate was evaporated down, and the solid which remained was recrystallized first from isopropanol and then from ethyl acetate/hexane. 1.0 g (8% of theory) of 1,4-dihydro-4-(ethylthiocarbamyl)-imino-1-phenylpyridazine was isolated as yellow crystals of melting point 134°-135° C.

Workup

  1. additionAfter the addition
  2. stirringstirred for a further 2 hours at room temperature
  3. filtrationfiltered
  4. customThe filtrate was evaporated down
  5. customthe solid which remained was recrystallized first from isopropanol

Sources & evidence

ORD record
ord-50fcdb2e9c7d4469a9efa81cc9363268
Source dataset
uspto-grants-1989_04
Patent number
US04820821

Reaction notes

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