Acryloyl chloride → {2-chloro-4-fluoro-5-[5-fluoro-2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-phenyl} acrylate

HRID 1193912Notes

Reaction equation

HRID 1193912 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[C:13]([F:16])=[C:12]([C:17]([F:20])([F:19])[F:18])[N:11]=[C:10]2[O:21][CH3:22])=[C:4]([F:23])[CH:3]=1.[C:24](Cl)(=[O:27])[CH:25]=[CH2:26].[H-].[Na+]>CN(C)C=O>[C:24]([O:8][C:7]1[CH:6]=[C:5]([N:9]2[C:14](=[O:15])[C:13]([F:16])=[C:12]([C:17]([F:20])([F:18])[F:19])[N:11]=[C:10]2[O:21][CH3:22])[C:4]([F:23])=[CH:3][C:2]=1[Cl:1])(=[O:27])[CH:25]=[CH2:26]

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 24758Sodium hydrideHCID 212707411-(4-chloro-2-fluoro-5-hydroxyphenyl)-5-fluoro-2-methoxy-4-trifluoromethyl-6(1H)-pyrimidinone

Product 1

HCID 54074081{2-chloro-4-fluoro-5-[5-fluoro-2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-phenyl} acrylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

using 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-5-fluoro-2-methoxy-4-trifluoromethyl-6(1H)-pyrimidinone and acryloyl chloride with sodium hydride in dimethylformamide there is obtained {2-chloro-4-fluoro-5-[5-fluoro-2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-phenyl} acrylate, 1H-NMR (CDCl3, 400 MHz): 7.42 ppm d,1H), 7.21 ppm (d,1H), 6.68 ppm (q,1H), 6.35 ppm (q,1H), 6.12 ppm (q,1H), 4.00 ppm (s,3H);

Sources & evidence

ORD record
ord-02055e0a80d34811a1dcd4b21f7e79b7
Source dataset
uspto-grants-1989_03
Patent number
US04812164

Reaction notes

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