Cyanuric chloride → 1,3-Diphenyl-1H-pyrazole-4-carbaldehyde

HRID 1929329Notes

Reaction equation

HRID 1929329 reaction equation
ClC1N=C(Cl)N=C(Cl)N=1.N1C=C[CH:13]=NN=1.[C:16]1([NH:22][N:23]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH3:25])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:32]([O-:35])([O-])=O.[Na+].[Na+]>CN(C=O)C>[C:16]1([N:22]2[CH:13]=[C:25]([CH:32]=[O:35])[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:23]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 7954Cyanuric chlorideHCID 10340Sodium CarbonateHCID 1230471,2,3-TriazineHCID 136372HCID 136372, compound

Product 1

HCID 5558201,3-Diphenyl-1H-pyrazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

2,4,6-Trichloro[1,3,5]triazine (1.83 g, 10.0 mmol) is added to DMF (2 mL), and maintained at 25° C. After the formation of a white solid, the reaction is monitored (TLC) until complete disappearance of the triazine. 1-Phenyl-2-(1-phenylethylidene)-hydrazine (1.0 g, 5.0 mmol) in DMF (15 mL) is added. After the addition, the mixture is then stirred at room temperature and monitored for completion (TLC) after which a 15% solution of Na2CO3 (20 mL) is added. The organic phase is extracted twice with 15 mL of diethyl ether. The organic layer is then dried (Na2SO4) and the solvent is removed in vacuo to afford the desired product. Yields of approximately 1.12 g (90%) of this product can be expected when the reaction is conducted on this scale. Mp 145° C.

Workup

  1. additionAfter the addition
  2. additionis added
  3. extractionThe organic phase is extracted twice with 15 mL of diethyl ether
  4. dry with materialThe organic layer is then dried (Na2SO4)
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-77c6f48336a9471a94afc1c9e17ff54d
Source dataset
uspto-grants-2012_05
Patent number
US08188080B2

Reaction notes

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