Methyl chloroglyoxylate → HCID 71208654, compound

HRID 1887828Notes

Reaction equation

HRID 1887828 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1.Cl[C:20](=[O:25])[C:21]([O:23][CH3:24])=[O:22]>C1(C)C=CC=CC=1>[CH3:24][O:23][C:21](=[O:22])[C:20]([N:12]([C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[C:8](=[O:11])[CH2:9][CH3:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:25]

Participants

4

Reactant 2

HCID 79846Methyl chloroglyoxylateHCID 71208293HCID 71208293, compound

Product 1

HCID 71208654HCID 71208654, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 1-(4-fluoro-2-phenylamino-phenyl)-propan-1-one (6.0 g, 24.7 mmol) in toluene (75 mL) was added methyl chlorooxoacetate (14.2 mL, 148 mmol) at room temperature under nitrogen. The reaction mixture was heated at reflux at 110° C. for 16 hr. The reaction mixture was concentrated under vacuum to afford N-(5-fluoro-2-propionyl-phenyl)-N-phenyl-oxalamic acid methyl ester. The crude product was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-4d9663461e394b7b9525502a46cbb910
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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