Ammonia → HCID 54316731, compound

HRID 1655177Notes

Reaction equation

HRID 1655177 reaction equation
[NH3:1].[C:2]([C:4]1[CH:5]=[N:6][N:7]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=2)[C:8]=1[CH:9]=[CH:10][C:11](Cl)=[O:12])#[N:3]>O1CCCC1.O>[C:2]([C:4]1[CH:5]=[N:6][N:7]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=2)[C:8]=1[CH:9]=[CH:10][C:11]([NH2:1])=[O:12])#[N:3]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 53679607HCID 53679607, compound

Product 1

HCID 54316731HCID 54316731, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred, ice-cold solution of 10 mL (0.15 mole) of concentrated aqueous ammonia in 15 mL of tetrahydrofuran was added dropwise a solution of 0.35 gram (0.001 mole) of 3-[4-cyano-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]acrylic acid chloride in 15 mL of tetrahydrofuran. Upon completion of the addition, the cooling bath was removed. The reaction vessel was closed by placing a rubber balloon over the open inlet of the reaction vessel. The reaction mixture was then allowed to warm to ambient temperature where it was stirred for one hour. After this time, the reaction mixture was concentrated at 45° C. under reduced pressure to a residual solid. The solid was triturated with petroleum ether and filtered, yielding a solid that did not completely melt at 212° C. The filtrate was concentrated in an air current, yielding a tan-yellow solid. Both solids were stirred in water separately. Each of the solids was then collected by filtration. The tan-yellow solid was triturated with two drops of isopropyl alcohol and petroleum ether. The suspension was cooled in a dry ice bath, and the solid was collected by filtration. The two solids were combined and dried, yielding 0.18 gram of 3-[4-cyano-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]- acrylamide, m.p. 208°-210° C., dec. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition
  2. customthe cooling bath was removed
  3. customThe reaction vessel was closed
  4. concentrationAfter this time, the reaction mixture was concentrated at 45° C. under reduced pressure to a residual solid
  5. customThe solid was triturated with petroleum ether
  6. filtrationfiltered
  7. customyielding a solid
  8. customthat did not completely melt at 212° C
  9. concentrationThe filtrate was concentrated in an air current,
  10. customyielding a tan-yellow solid
  11. filtrationEach of the solids was then collected by filtration
  12. customThe tan-yellow solid was triturated with two drops of isopropyl alcohol and petroleum ether
  13. temperatureThe suspension was cooled in a dry ice bath
  14. filtrationthe solid was collected by filtration
  15. customdried

Sources & evidence

ORD record
ord-be071230e39b44a597c109e97eb7447e
Source dataset
uspto-grants-1993_10
Patent number
US05250504

Reaction notes

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