Chloroacetyl chloride → HCID 46899457, compound

HRID 2068827Notes

Reaction equation

HRID 2068827 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH2:13][NH2:14])[CH:3]=1.[Cl:15][CH2:16][C:17](Cl)=[O:18].CCCCCC.C([O-])(O)=O.[Na+]>C(Cl)Cl.C(OCC)(=O)C>[Cl:15][CH2:16][C:17]([NH:14][CH2:13][C:4]1[CH:3]=[C:2]([CH3:1])[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=1)=[O:18]

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8058HexaneHCID 516892Sodium BicarbonateHCID 68586856HCID 68586856, compound

Product 1

HCID 46899457HCID 46899457, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Methyl-3-aminomethyl-1-phenylpyrazole (2.434 g, 15 mmol) was dissolved in 20 mL of purified methylene chloride, dropwisely added with chloroacetyl chloride (1.194 mL, 15 mmol) at 0° C. and then stirred at room temperature. Completion of the reaction was confirmed by TLC (hexane:ethyl acetate=1:1). Upon completion of reaction, the reaction mixture was adjusted to pH 7 using saturated aq. NaHCO3 and then extracted with methylene chloride. The resulting organic layer was dried with anhydrous magnesium sulfate and filtered, and the filtrate was concentrated and dried in vacuo to obtain the title compound, 3-(2-chloroacetamido)methyl-1-phenyl-5-methylpyrazole.

Workup

  1. customUpon completion of reaction
  2. extractionextracted with methylene chloride
  3. dry with materialThe resulting organic layer was dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-4e1099ccd3384c40afae55269979e80d
Source dataset
uspto-grants-2012_10
Patent number
US08299072B2

Reaction notes

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