Potassium Carbonate → HCID 15337899, compound

HRID 2396320Notes

Reaction equation

HRID 2396320 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH3:22])=[O:20]>CN(C)C=O.C(OCC)(=O)C>[C:19]([CH2:18][NH:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])([O:21][CH3:22])=[O:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate2×HCID 170059Benzonitrile, 2-amino-4-chloro-

Product 1

HCID 15337899HCID 15337899, compoundYield 36.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 2-amino-4-chlorobenzonitrile (12.9 g, 85 mmol) in anhydrous dimethylformamide (15 mL). Add potassium carbonate (7.6 g, 90 mmol) and methyl bromoacetate (7.8 mL, 90 mmol) and stir at 70° C. for 5 days. Add additional methyl bromoacetate (78 mL, 90 mmol) and continue heating for 1 day. Dilute with ethyl acetate (300 mL), wash with water, separate the organic phase and dry (MgSO4). Evaporate the solvent in vacuo and purify by flash chromatography (25% ethyl acetate/hexane). Recrystallize (hexane) to give the title compound (7 g, 36%).

Workup

  1. temperaturecontinue heating for 1 day
  2. washwash with water
  3. customseparate the organic phase
  4. dry with materialdry (MgSO4)
  5. customEvaporate the solvent in vacuo
  6. custompurify by flash chromatography (25% ethyl acetate/hexane)
  7. customRecrystallize (hexane)

Sources & evidence

ORD record
ord-82bc4cc28a4d4afe93c52494181ff9ea
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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