Hydrochloric Acid → HCID 73654000, compound

HRID 1655179Notes

Reaction equation

HRID 1655179 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=2)[C:7]=1[CH:8]=[CH:9][C:10](Cl)=[O:11])#[N:2].[CH3:24][C:25](=[N:27][OH:28])[CH3:26].C(N(CC)CC)C.Cl>O1CCCC1.CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1.O>[C:1]([C:3]1[CH:4]=[N:5][N:6]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=2)[C:7]=1[CH:8]=[CH:9][C:10]([O:28][N:27]=[C:25]([CH3:26])[CH3:24])=[O:11])#[N:2]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 67180Acetone, oximeHCID 53679607HCID 53679607, compound

Product 1

HCID 73654000HCID 73654000, compoundYield 25.1%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

At 30° C. solution of 0.6 gram (0.002 mole) of 3-[4-cyano-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]acrylic acid chloride in 15 mL of tetrahydrofuran was added in portions to a stirred solution of 0.2 gram (0.002 mole) of acetone oxime, 0.3 gram (0.003 mole) of triethylamine, and a catalytic amount of 4-dimethylaminopyridine in 35 mL of toluene. Upon completion of the addition, the reaction mixture was stirred at 30° C. for five hours. After this time, the reaction mixture was diluted with water, and the pH was adjusted to about 3.0 with concentrated hydrochloric acid. The organic layer was separated and washed with an aqueous sodium chloride solution and then with water. The organic layer was concentrated under reduced pressure to a residual solid. The solid was subjected to column chromatography on silica gel with 1:1 hexane/ethyl acetate as eluant. Those fractions found by thin layer chromatography to contain a major constituent other than eluent and starting materials were combined and concentrated at 40° C. under reduced pressure, yielding 0.2 gram of isopropylideneamino 3-[4-cyano-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]acrylate. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition
  2. customThe organic layer was separated
  3. washwashed with an aqueous sodium chloride solution
  4. concentrationThe organic layer was concentrated under reduced pressure to a residual solid
  5. concentrationconcentrated at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-8190c6adf5f64f8cb4bd4f3ffc2e4ac5
Source dataset
uspto-grants-1993_10
Patent number
US05250504

Reaction notes

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