Hydrochloric Acid → 2-(2-Phenyl-5-ethyl-1,2,3-triazol-4-yl)-3-(1,3,4-trimethyl-5-pyrazolyl)-3-oxopropionitrile

HRID 1096681Notes

Reaction equation

HRID 1096681 reaction equation
[C:1]1([N:7]2[N:11]=[C:10]([CH2:12][C:13]#[N:14])[C:9]([CH2:15][CH3:16])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:19][C:20]([C:22]1[N:26]([CH3:27])[N:25]=[C:24]([CH3:28])[C:23]=1[CH3:29])=O)C.C(OCCOCCO)C.[Na].Cl>O.COCCOCCOC.CCCCCCC>[O:19]=[C:20]([C:22]1[N:26]([CH3:27])[N:25]=[C:24]([CH3:28])[C:23]=1[CH3:29])[CH:12]([C:10]1[C:9]([CH2:15][CH3:16])=[N:8][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:11]=1)[C:13]#[N:14]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8146Diethylene Glycol Monoethyl EtherHCID 5360545SodiumHCID 9855653Ethyl 1,3,4-trimethyl-1H-pyrazole-5-carboxylateHCID 18002320(5-Ethyl-2-phenyl-2H-1,2,3-triazol-4-yl)acetonitrile

Product 1

HCID 667812552-(2-Phenyl-5-ethyl-1,2,3-triazol-4-yl)-3-(1,3,4-trimethyl-5-pyrazolyl)-3-oxopropionitrileYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8150DiglymeSolventHCID 8900HeptaneSolvent

Conditions

Temperature
92.5 °C

Procedure

In a 2 L-reaction flask equipped with a rectification column, 116.7 g (0.55 mol) of 2-phenyl-4-cyanomethyl-5-ethyl-1,2,3-triazole, 91 g (0.5 mol) of 1,3,4-trimethylpyrazol-5-carboxylic acid ethyl ester, 900 g of heptane, 60 g of diethylene glycol dimethyl ether, and 30 g of diethylene glycol monoethyl ether were added, then azeotropic dehydration was carried out by heating at 90 to 95° C., thereafter 115.5 g (0.6 mol) of 28% sodium was added dropwise over 10 hours, and the resulting mixture was reacted for 7 hours. After cooling to 30° C. or less, 3000 g of water was added to separate out heptane phase, and further the aqueous phase was washed with 600 g of heptane, the heptane phase was separated out, 900 g of xylene was added, then 62.5 g (0.6 mol) of 35% hydrochloric acid was added dropwise to be neutralized. The aqueous phase was separated out, washed with 600 g of water two times, the aqueous phase was separated out to obtain a xylene solution containing 156.8 g (yield 90%) of 3-oxo-2-(2-phenyl-5-ethyl-1,2,3-triazol-4-yl)-3-(1,3,4-trimethylpyrazol-5-yl) propionitrile.

Workup

  1. customIn a 2 L-reaction flask
  2. additionwere added
  3. customthe resulting mixture was reacted for 7 hours
  4. temperatureAfter cooling to 30° C. or less
  5. customto separate out heptane phase
  6. washfurther the aqueous phase was washed with 600 g of heptane
  7. customthe heptane phase was separated out
  8. addition900 g of xylene was added
  9. customThe aqueous phase was separated out
  10. washwashed with 600 g of water two times
  11. customthe aqueous phase was separated out
  12. customto obtain a xylene solution

Sources & evidence

ORD record
ord-690d30904d514e25ad08d509706787ef
Source dataset
uspto-grants-2012_03
Patent number
US08138368B2

Reaction notes

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