Methyl chloroacetate → HCID 67257240, compound

HRID 1771987Notes

Reaction equation

HRID 1771987 reaction equation
[NH2:1][N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]1=[NH2+:9].CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[Cl:23][CH2:24][C:25](OC)=O.C(=O)([O-])[O-].[K+].[K+]>CCO>[Cl:23][CH2:24][C:25]1[N:9]=[C:3]2[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][N:2]2[N:1]=1

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 178425976HCID 178425976, compound

Product 1

HCID 67257240HCID 67257240, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1-amino-3-methylpyridin-2(1H)-iminium-2,4,6-trimethylbenzenesulfonate (630 mg, crude product from the previous step, 1.95 mmol), methyl 2-chloroacetate (423 mg, 3.90 mmol) and potassium carbonate (540 mg, 3.9 mmol) in EtOH (10 mL) was stirred at 80° C. for 4 h. After cooled to room temperature, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (eluting with 25% v/v EtOAc in PE) to give the title compound (95 mg, yield 27%). ESI MS: m/z 182, 184 [M+H]+.

Workup

  1. temperatureAfter cooled to room temperature
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (
  4. washeluting with 25% v/v EtOAc in PE)

Sources & evidence

ORD record
ord-ded6d0e69bc044599887a1c4a8b0e988
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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