Реакция #65080

Уравнение реакции

sodium methoxide

ethyl 3-amino-4,4,4-trifluorocrotonate

ethyl 4-chloro-5-ethylsulfonylamino-2-fluorocarbanilate

→

objective product

Выход 77.0%

3-(4-chloro-5-ethylsulfonylamino-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Выход 77.0%

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   Другоеreacted for 4 hours
2. 2
   workup.DISTILLATIONN,N-dimethylformamide was distilled off
3. 3
   workup.DISSOLUTIONthe resultant product was dissolved in water
4. 4
   ПромывкаThe thus-obtained solution was washed with diethyl ether 3 times
5. 5
   workup.ADDITIONconcentrated hydrochloric acid was added
6. 6
   ФильтрацияThe precipitated crystals were filtered out
7. 7
   Промывкаwashed with water
8. 8
   Другоеdried

Методика

1.06 g (5.77 mmol) of ethyl 3-amino-4,4,4-trifluorocrotonate was dissolved in 6.2 ml of N,N-dimethylformamide and 0.82 g (14.4 mmol) of sodium methoxide was added thereto. The reaction mixture was cooled to not higher than 5° C. after 10 minutes, and 1.56 g (4.81 mmol) of ethyl 4-chloro-5-ethylsulfonylamino-2-fluorocarbanilate was added thereto. The resultant mixture was heated to 110° C. and reacted for 4 hours. After the reaction was completed, N,N-dimethylformamide was distilled off and the resultant product was dissolved in water. The thus-obtained solution was washed with diethyl ether 3 times and thereafter concentrated hydrochloric acid was added thereto to pH 2. The precipitated crystals were filtered out, washed with water and dried to obtain 1.54 g of the objective product (yield: 77%) in the form of light yellow crystals.

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