Ethyl Acetoacetate → HCID 70395142, compound

HRID 1722938Notes

Reaction equation

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

Participants

Reactant 2

HCID 8868Ethyl Acetoacetate

HCID 177702854-Chloro-2-fluoro-5-isopropoxyphenylurea

Product 1

HCID 70395142HCID 70395142, compound

Procedure

from 4-chloro-2-fluoro-5-isopropoxyphenylurea and ethyl acetoacetate using finely powdered Amberlyst®-15 (an organic, polymeric resin having free sulphonyl groups) as the catalyst there is obtained ethyl 3-[3-(4-chloro-2-fluoro-5-isopropoxyphenyl)ureido]crotonate, m.p. 142°-144° C. and from this intermediate in dimethylformamide with sodium hydride there is obtained 3-(4-chloro-2-fluoro-5-isopropoxyphenyl)-6 -methyl-2,4(1H,3H)-pyrimidinedione, m.p. 228°-230° C.;

Sources & evidence

ORD record: ord-6a4cf12e199f4d1cab0a16c60a1e7fb2
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04859229

Reaction notes

Loading…