Benzylamine → HCID 19783052, compound

HRID 257324Notes

Reaction equation

HRID 257324 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[C:9](Cl)[N:8]=2)[N:5]=[CH:4][C:3]=1[C:19]#[N:20].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1.C(Cl)Cl>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[C:9]([NH:28][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:8]=2)[N:5]=[CH:4][C:3]=1[C:19]#[N:20]

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 18689500HCID 18689500, compound

Product 1

HCID 19783052HCID 19783052, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 6.0 grams (0.019 mole) of 5-amino- 1-(3,6-dichloro-5-trifluoromethylpyridin-2-yl)-4-cyanopyrazole and 15.4 grams (0.144 mole) of benzylamine in 100 mL of tetrahydrofuran was heated at reflux for 3.5 hours. The reaction mixture was cooled and filtered. The filtrate was evaporated under reduced pressure, leaving a residue. This residue was dissolved in methylene chloride, and the organic solution was washed in succession with water, dilute hydrochloric acid, and water. The washed organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure, leaving a pale yellow solid residue. This residue, in 200 mL of petroleum ether, was heated to reflux and then allowed to cool to room temperature. The mixture was filtered, and the filter cake was dried to yield 3.0 grams of 5-amino-1-(3-chloro-5-trifluoromethyl-6-phenylmethylaminopyridin-2-yl)-4-cyanopyrazole. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for 3.5 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure
  5. customleaving a residue
  6. washthe organic solution was washed in succession with water, dilute hydrochloric acid, and water
  7. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated under reduced pressure
  10. customleaving a pale yellow solid residue
  11. temperatureto reflux
  12. filtrationThe mixture was filtered
  13. customthe filter cake was dried

Sources & evidence

ORD record
ord-ba2a81f0c8574d1f856b01418f3f1cca
Source dataset
uspto-grants-1993_11
Patent number
US05262382

Reaction notes

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