Ethyl 3-amino-2-ethylcrotonate → Ethyl 2-ethyl-3-[3-(4-chloro-2-fluoro-5-isopropoxyphenyl)ureido]-crotonate

HRID 1722941Notes

Reaction equation

HRID 1722941 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([N:12]=[C:13]=[O:14])=[C:4]([F:15])[CH:3]=1.[NH2:16]/[C:17](/[CH3:26])=[C:18](/[CH2:24][CH3:25])\[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O>[CH2:24](/[C:18](=[C:17](/[NH:16][C:13]([NH:12][C:5]1[CH:6]=[C:7]([O:8][CH:9]([CH3:10])[CH3:11])[C:2]([Cl:1])=[CH:3][C:4]=1[F:15])=[O:14])\[CH3:26])/[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:25]

Participants

4

Reactant 2

HCID 10630766Ethyl 3-amino-2-ethylcrotonateHCID 132729244-Chloro-2-fluoro-5-isopropoxyphenyl isocyanate

Product 1

HCID 70395854Ethyl 2-ethyl-3-[3-(4-chloro-2-fluoro-5-isopropoxyphenyl)ureido]-crotonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

using 4-chloro-2-fluoro-5-isopropoxyphenyl isocyanate in dimethylformamide with ethyl 3-amino-2-ethylcrotonate there is obtained ethyl 2-ethyl-3-[3-(4-chloro-2-fluoro-5-isopropoxyphenyl)ureido]-crotonate, m.p. 112°-114° C. and from this intermediate with sodium hydride in dimethylformamide there is obtained 5-ethyl-3-(4-chloro-2-fluoro-5-isopropoxyphenyl)-6-methyl-2,4(1H,3H)-pyrimidinedione, m.p. 128°-130° C.

Sources & evidence

ORD record
ord-408464ca3ef44bdfb2f5103ae0bc6498
Source dataset
uspto-grants-1989_08
Patent number
US04859229

Reaction notes

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