4-Chloro-2-fluoro-5-isopropoxyphenyl isocyanate → Ethyl 3-[3-(4-chloro-2-fluoro-5-isopropoxyphenyl)ureido]-2-methyl-2-pentenoate

HRID 1722940

Reaction equation

HRID 1722940 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]([CH2:25][CH3:26])=[C:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(OCC)C>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:10])[CH3:11])=[CH:6][C:5]([NH:12][C:13](=[O:14])[NH:16][C:17]([CH2:25][CH3:26])=[C:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:4]([F:15])[CH:3]=1

Participants

4

Reactant 2

HCID 132729244-Chloro-2-fluoro-5-isopropoxyphenyl isocyanateHCID 86743319Ethyl 3-amino-2-methyl-2-pentenoate

Product 1

HCID 53742260Ethyl 3-[3-(4-chloro-2-fluoro-5-isopropoxyphenyl)ureido]-2-methyl-2-pentenoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

using 4-chloro-2-fluoro-5-isopropoxyphenyl isocyanate in diethyl ether with ethyl 3-amino-2-methyl-2-pentenoate there is obtained ethyl 3-[3-(4-chloro-2-fluoro-5-isopropoxyphenyl)ureido]-2-methyl-2-pentenoate, m.p. 104°-106° C., and from this intermediate with sodium hydride in dimethylformamide there is obtained 6-ethyl-3-(4-chloro-2-fluoro-5-isopropoxyphenyl)-5 -methyl-2,4(1H,3H)-pyrimidinedione, m.p. 196°-198° C.:

Sources & evidence

ORD record
ord-163eb66e38d7440fbc7a6966e69df8c0
Source dataset
uspto-grants-1989_08
Patent number
US04859229

Linked notes

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