N,N'-Dimethylurea → 2-amino-4-fluoro-N-methylbenzamide

HRID 255301

Reaction equation

HRID 255301 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH3:12][NH:13]C(NC)=O>O>[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:13][CH3:12])=[O:5]

Participants

4

Reactant 2

HCID 7293N,N'-DimethylureaHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 569516612-amino-4-fluoro-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-amino 4-fluoro benzoic acid (2.5 g, 16.13 mmol) and 1,3 dimethyl urea (5.85 g, 66.5 mmol) was heated at 150° C. for 24 hours. The reaction was diluted with water, filtered and extracted twice with ethyl acetate. The organic extracts were dried over magnesium sulfate and concentrated at reduced pressure. Chromatography on silica gel with ethyl acetate in hexanes (0-50%) gave the title compound as a waxy solid (670 mg, 25%)

Workup

  1. filtrationfiltered
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe organic extracts were dried over magnesium sulfate
  4. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-98808f368c2d4988b537d19cf74e01c2
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Linked notes

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