Urea derivative and process for producing the same
A technology of compound and hydrogen atom, which is applied in the field of preparation of urea derivatives, can solve the problems of useful intermediates and other effective preparation methods of urea compounds that are not disclosed
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[0061] The preparation method of the present invention will be described in detail below.
[0062] Preparation method 1 The preparation method of urea (A-1)
[0063]
[0064] [In the formula, each symbol has the same meaning as above. ]
[0065] [Step 1-1]
[0066] This step is a step in which compound (A-2) is obtained by reacting a carbamate-forming reagent (A-3) such as phenyl chloroformate with compound (A-4). As the reaction solvent, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, tetrahydrofuran, ethyl acetate and the like can be used. A base such as pyridine can also be used in the reaction. 1 to 2 equivalents of the carbamate reagent (A-3) can be used with respect to the compound (A-4). 1 to 5 equivalents of the base can be used with respect to the compound (A-4). The reaction time is 10 minutes to 30 hours. The reaction temperature is from 0°C to heating reflux temperature, preferably from 0°C to room temperature.
[0067] [Step 1-2]
[...
Embodiment 1
[0077] (Example 1) N-(2-chloro-4-hydroxyphenyl) phenyl carbamate
[0078]
[0079] Suspend 4-amino-3-chlorophenol (23.7g) in N,N-dimethylformamide (100mL), add pyridine (23.4mL) under ice-cooling, and drop in at 20°C or below Phenyl chloroformate (23.2 mL). After stirring at room temperature for 30 minutes, water (400 mL), ethyl acetate (300 mL), 6N-HCl (48 mL) were added, and the organic layer was separated after stirring. The organic layer was washed twice with 10% brine (200 mL), and dried over magnesium sulfate. The solvent was distilled off to obtain 46 g of the title compound as a solid.
[0080] 1 H-NMR (CDCl 3 ): 5.12 (1h, br s), 6.75 (1H, dd, J=9.2, 2.8Hz), 6.92 (1H, d, J=2.8Hz), 7.18-7.28 (4H, m), 7.37-7.43 (2H , m), 7.94 (1H, br s)
Embodiment 2
[0081] (Example 2) 1-(2-chloro-4 hydroxyphenyl)-3-cyclopropylurea
[0082]
[0083] Dissolve phenyl N-(2-chloro-4-hydroxyphenyl)carbamate in N,N-dimethylformamide (100mL), add cyclopropylamine (22.7mL) under ice cooling, and stir at room temperature overnight. Water (400 mL), ethyl acetate (300 mL), 6N-HCl (55 mL) were added, stirred and the organic layer was separated. The organic layer was washed twice with 10% brine (200 mL), and dried over magnesium sulfate. After washing with heptane, the prisms obtained by concentrating the solvent were filtered to obtain 22.8 g of the title compound. (77% yield from 4-amino-3-chlorophenol)
[0084] 1 H-NMR (CDCl 3 ): 0.72-0.77 (2H, m), 0.87-0.95 (2H, m), 2.60-2.65 (1H, m), 4.89 (1H, br s), 5.60 (1H, br s), 6.71 (1H, dd , J=8.8, 2.8Hz), 6.88 (1H, d, J=2.8Hz), 7.24-7.30 (1H, br s), 7.90 (1H, d, J=8.8H)
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