Ethyl chloroformate → 1-ethoxycarbonyl-3-(4-chloro-2-fluoro-5-isopropoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 1722954Notes

Reaction equation

HRID 1722954 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[NH:14][C:13]2=[O:23])=[C:4]([F:24])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:32]([O:34][CH2:35][CH3:36])=[O:33]>CC(C)=O>[CH2:35]([O:34][C:32]([N:14]1[C:15]([C:19]([F:22])([F:21])[F:20])=[CH:16][C:17](=[O:18])[N:12]([C:5]2[CH:6]=[C:7]([O:8][CH:9]([CH3:11])[CH3:10])[C:2]([Cl:1])=[CH:3][C:4]=2[F:24])[C:13]1=[O:23])=[O:33])[CH3:36]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 114285773-(4-chloro-2-fluoro-5-isopropoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 200259511-ethoxycarbonyl-3-(4-chloro-2-fluoro-5-isopropoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

using 3-(4-chloro-2-fluoro-5-isopropoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione with potassium carbonate and ethyl chloroformate in acetone there is obtained 1-ethoxycarbonyl-3-(4-chloro-2-fluoro-5-isopropoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, 1H-NMR (CDCl3, 400 MHz): 7.30 ppm (d,1H), 6.83 ppm (d,1H), 6.37 ppm (s,1H), 4.51 ppm (q,2H), 4.45 ppm (m,1H), 1.42 ppm (t,3H), 1.37 ppm (d,6H);

Sources & evidence

ORD record
ord-caa61220aa1244f2b85da086f0c47421
Source dataset
uspto-grants-1989_08
Patent number
US04859229

Reaction notes

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