반응 #467496

반응 방정식

4-chloro-2-fluoro-5-isopropyloxyphenylisocyanate

2,4-dinitrophenoxyamine

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

sodium hydride

→

1-Amino-3-(4-chloro-2-fluoro-5-isopropyloxyphenyl)-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

용매

toluene

N,N-dimethylformamide

N,N-dimethylformamide

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGThe solution was stirred at room temperature for 2 hours
3. 3
   workup.STIRRINGStirring
4. 4
   workup.WAITwas continued for 3 days
5. 5
   기타gave a solid which
6. 6
   기타was chromatographed on silica gel eluting with ethyl acetate
7. 7
   workup.ADDITIONhexane, 1:5, containing 0.1% of triethylamine

실험 절차

A suspension of sodium hydride (10 g, 60% in oil) in N,N-dimethylformamide (30 ml) was stirred at 0° C. under nitrogen while a solution of ethyl 3-amino-4,4,4-trifluorocrotonate (4.5 g) in N,N-dimethylformamide (20 ml) was added dropwise. After stirring for 15 minutes, a solution of 4-chloro-2-fluoro-5-isopropyloxyphenylisocyanate (5.6 g) in toluene (25 ml) was added slowly at -35° C. The solution was stirred at room temperature for 2 hours and treated with a solution of 2,4-dinitrophenoxyamine (5.8 g) in N,N-dimethylformamide (20 ml). Stirring was continued for 3 days. The solution was processed and gave a solid which was chromatographed on silica gel eluting with ethyl acetate:hexane, 1:5, containing 0.1% of triethylamine. 1-Amino-3-(4-chloro-2-fluoro-5-isopropyloxyphenyl)-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione was obtained as a white solid (5.3 g).

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