1,2-Dichloroethane → Epyrifenacil

HRID 1372360Notes

Reaction equation

HRID 1372360 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]2=[O:29])=[CH:12][C:3]=1[O:4][C:5]1[C:6](=[O:11])[NH:7][CH:8]=[CH:9][CH:10]=1.FC(F)(F)S(O)(=O)=O.ClCCCl.[N+](=[CH:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])=[N-]>CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]2=[O:29])=[CH:12][C:3]=1[O:4][C:5]1[C:6]([O:11][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 12192Ethyl diazoacetateHCID 62406Trifluoromethanesulfonic acidHCID 116549103-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]-1H-pyridin-2-one

Product 1

HCID 12097345Epyrifenacil

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Into a mixture of 1.0 g of 3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]-1H-pyridin-2-one, 70 mg of trifluoromethanesulfonic acid and 40 ml of 1,2-dichloroethane, 0.4 ml of ethyl diazoacetate (purity: 90%) is dropped at room temperature over 2 hours. After dropping, the reaction mixture is further stirred for 2 hours, and subjected to silica gel column chromatography (eluent; hexane/ethyl acetate=2/1) to give 3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]-2-(ethoxycarbonylmethoxy)pyridine.

Workup

  1. additionis dropped at room temperature over 2 hours

Sources & evidence

ORD record
ord-7335f8f701494539b73a60d2e2a2bfe9
Source dataset
uspto-grants-2007_01
Patent number
US07157579B2

Reaction notes

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