Water → HCID 54079011, compound

HRID 1679243Notes

Reaction equation

HRID 1679243 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][NH2:10].S(F)([O-])(=O)=O.[CH2:16]([O:18][C:19](=[O:29])[CH2:20][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C:22]1=C[OH2+])[CH3:17].O.[OH-].[K+]>C(Cl)Cl>[CH2:16]([O:18][C:19](=[O:29])[CH2:20][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C:22]1=[N:10][NH:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 408929(2,4-Dichlorophenyl)hydrazineHCID 86735552HCID 86735552, compound

Product 1

HCID 54079011HCID 54079011, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 17.7 parts of 2,4-dichlorophenylhydrazine in methylene chloride was added dropwise to the above reaction mixture containing [1-(2-ethoxy-2-oxoethyl)piperidin-2-ylidene]methyloxonium fluorosulfate while keeping the temperature of the reaction less than 30° C. After the addition was completed the reaction was stirred for an additional 30 minutes. The reaction mass was then poured into 1000 parts of water. The pH was raised to 12.0 with 20% potassium hydroxide solution. The crude product was extracted with three successive portions of 1000 parts of methylene chloride. The organic extracts of the product were dried over anhydrous sodium sulfate. The solution of the product was filtered to remove the drying agent. The solvent was removed at a reduced pressure of 50-300 mm with a rotary evaporator leaving the crude product which was used in the next step without further purification.

Workup

  1. customthe temperature of the reaction less than 30° C
  2. additionAfter the addition
  3. extractionThe crude product was extracted with three successive portions of 1000 parts of methylene chloride
  4. dry with materialThe organic extracts of the product were dried over anhydrous sodium sulfate
  5. filtrationThe solution of the product was filtered
  6. customto remove the drying agent
  7. customThe solvent was removed at a reduced pressure of 50-300 mm with a rotary evaporator

Sources & evidence

ORD record
ord-48e4c74b48834ffc90fbc9107f83030d
Source dataset
uspto-grants-1978_03
Patent number
US04080192

Reaction notes

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