Sodium hydride → 3-[Ethyl-(2-hydroxypropyl)amino]-6-triphenylmethylazopyridazine

HRID 482793Notes

Reaction equation

HRID 482793 reaction equation
[H-].[Na+].[CH2:3]([NH:5][CH2:6][CH:7]([OH:9])[CH3:8])[CH3:4].Cl[C:11]1([N:36]=[N:37][C:38]2[N:39]=[N:40][CH:41]=[CH:42][CH:43]=2)[CH:16]=[CH:15][C:14]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:13][NH:12]1>O1CCCC1>[CH2:3]([N:5]([CH2:6][CH:7]([OH:9])[CH3:8])[C:11]1([N:36]=[N:37][C:38]2[N:39]=[N:40][CH:41]=[CH:42][CH:43]=2)[CH:16]=[CH:15][C:14]([C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:13][NH:12]1)[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 30161641-(Ethylamino)propan-2-olHCID 67909128HCID 67909128, compound

Product 1

HCID 704550993-[Ethyl-(2-hydroxypropyl)amino]-6-triphenylmethylazopyridazineYield 77.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 50% suspension of 1.5 g sodium hydride in 100 ml tetrahydrofuran, 3 g ethyl-(2-hydroxypropyl)amine are added; this is stirred at room temperature for 30 minutes, thereafter 4.5 g of 3-chloro-6-triphenylmethylazopyridazine are added. Stirring is maintained for 5 minutes, the organic phase is washed with a saturated solution of sodium chloride, rendered anhydrous and evaporated to dryness under a vacuum. The residue is taken up with ethyl alcohol, diluted with water, and the precipitate is collected under a vacuum which is then triturated with diisopropyl ether to yield 4 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-triphenylmethylazopyridazine melting at 137° C. (with decomposition). A solution of 3 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-triphenylmethylazopyridazine in 300 ml ethyl alcohol and 50 ml tetrahydrofuran containing 300 mg 5% palladium on carbon is hydrogenated at room temperature and pressure. The catalyst is filtered out, then the residue is evaporated and triturated with diethyl ether to yield 2.5 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-(2-triphenylmethylhydrazino)pyridazine melting at 122° C. (with decomposition). A solution of 2 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-(2-triphenylmethylhydrazino)pyridazine in 100 ml absolute ethyl alcohol is mixed with 2.5 ml concentrated hydrochloric acid and stirred for 15 minutes at room temperature. This is evaporated under a vacuum and the residue taken up with isopropyl alcohol. This is diluted with diisopropyl ether to yield 1.2 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-hydrazinopyridazine dihydrochloride melting at 208°-212° C. (with decomposition).

Workup

  1. stirringStirring
  2. temperatureis maintained for 5 minutes
  3. washthe organic phase is washed with a saturated solution of sodium chloride
  4. customevaporated to dryness under a vacuum
  5. additiondiluted with water
  6. customthe precipitate is collected under a vacuum which
  7. customis then triturated with diisopropyl ether

Sources & evidence

ORD record
ord-56194b254c304412b99641c6a70b62cc
Source dataset
uspto-grants-1986_03
Patent number
US04575552

Reaction notes

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