N,N'-Dimethylurea → 2-amino-4-fluoro-N-methylbenzamide
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
Product 1
Reagents, catalysts & solvents 1
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
- filtrationfiltered
- extractionextracted twice with ethyl acetate
- dry with materialThe organic extracts were dried over magnesium sulfate
- concentrationconcentrated at reduced pressure
Sources & evidence
- ORD record
- ord-ccf5bdd867734bd09098edab0723fa3c
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08124602B2
Reaction notes
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