m-Toluamide → HCID 57804321, compound

HRID 2103419Notes

Reaction equation

HRID 2103419 reaction equation
Cl[CH:2]([C:7]([CH3:9])=O)[C:3]([O:5][CH3:6])=[O:4].[CH3:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([NH2:16])=[O:15]>C(OCC)(=O)C>[CH3:6][O:5][C:3]([C:2]1[O:15][C:14]([C:13]2[CH:12]=[C:11]([CH3:10])[CH:19]=[CH:18][CH:17]=2)=[N:16][C:7]=1[CH3:9])=[O:4]

Participants

4

Reactant 2

HCID 69253m-ToluamideHCID 107332Methyl 2-chloroacetoacetate

Product 1

HCID 57804321HCID 57804321, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Heat to 120° C. a neat mixture of methyl 2-chloroacetoacetate (914 mL, 7.5 mmol) and 3-methyl-benzamide (676 mg, 5 mmol) and stir at this temperature for 12 hrs. Cool the reaction mixture to room temperature and dilute it with ethyl acetate, wash with saturated sodium bicarbonate solution (3 times), water (twice) and brine, Dry the organic extract over MgSO4 and concentrate. Purify the resulting residue by flash chromatography (elute with 10% ethyl acetate in heptane) to give the title compound as a yellow oil (492 mg).

Workup

  1. temperatureCool the reaction mixture to room temperature
  2. washwash with saturated sodium bicarbonate solution (3 times), water (twice) and brine
  3. customDry the
  4. extractionorganic extract over MgSO4
  5. concentrationconcentrate
  6. customPurify the resulting residue
  7. washby flash chromatography (elute with 10% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-99426b917f9e47219be76096d3de44bd
Source dataset
uspto-grants-2009_08
Patent number
US07576109B2

Reaction notes

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