Potassium Carbonate → HCID 15580736, compound

HRID 543802Notes

Reaction equation

HRID 543802 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:14]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:17][CH:18]=2)[N:9]=1.[Br:23][CH:24]([CH3:28])[C:25](Cl)=[O:26]>C(Cl)(Cl)Cl>[Br:23][CH:24]([CH3:28])[C:25]([NH:7][C:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:14]=[C:15]([C:19]([F:20])([F:22])[F:21])[CH:16]=[CH:17][CH:18]=2)[N:9]=1)=[O:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 477954,5-Dihydro-1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-amineHCID 979802-Bromopropanoyl chloride

Product 1

HCID 15580736HCID 15580736, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 100 ml. of chloroform with stirring is added 2.75 g. of potassium carbonate and 5.3 g. of 3-amino-1-(α,α,α-trifluoro-m-tolyl)-2-pyrazoline, then 5.0 g. of α-bromopropionylchloride is added dropwise. After the addition is complete the reaction mixture is refluxed on a steam bath for 4 hours. Then the solvent is removed in vacuo and water is added to give a gum. The gum is extracted with dichloromethane. The extracts are combined and dried over anhydrous magnesium sulfate. The solution is passed through a short column of a hydrous magnesium silicate, then is evaporated leaving a gummy solid. The solid is triturated with ether to give 1.13 g. of a yellow solid. The solid is recrystallized from acetone-hexane to give the desired product as yellow crystals, m.p. 54°-56° C.

Workup

  1. additionis added 2.75 g
  2. additionAfter the addition
  3. temperatureis refluxed on a steam bath for 4 hours
  4. customThen the solvent is removed in vacuo and water
  5. additionis added
  6. customto give a gum
  7. extractionThe gum is extracted with dichloromethane
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customis evaporated
  10. customleaving a gummy solid
  11. customThe solid is triturated with ether
  12. customto give 1.13 g
  13. customThe solid is recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-36cf72e47f3944798f17b7101d231b09
Source dataset
uspto-grants-1984_05
Patent number
US04447442

Reaction notes

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