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Hydrochloric Acid → Epyrifenacil

HRID 1862337
Notes
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Reaction equation

HRID 1862337 reaction equation
N(OCCC(C)C)=O.N[C:10]1[CH:29]=[C:28]([F:30])[C:27]([N:31]2[C:36](=[O:37])[CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[N:33]([CH3:42])[C:32]2=[O:43])=[CH:26][C:11]=1[O:12][C:13]1[C:14]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:15][CH:16]=[CH:17][CH:18]=1.[ClH:44]>C(#N)C.[Cu]Cl.[Cu](Cl)Cl>[Cl:44][C:10]1[CH:29]=[C:28]([F:30])[C:27]([N:31]2[C:36](=[O:37])[CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[N:33]([CH3:42])[C:32]2=[O:43])=[CH:26][C:11]=1[O:12][C:13]1[C:14]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:15][CH:16]=[CH:17][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 186191543-{2-Amino-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(ethoxycarbonyl)methoxypyridine

Product 1

HCID 12097345Epyrifenacil

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalyst
HCID 62652Cuprous chlorideCatalyst
HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 10.99 g of isoamyl nitrite in 10 ml of acetonitrile was added to a mixture of 15.46 g of 3-{2-amino-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(ethoxycarbonyl)methoxypyridine, 6.19 g of copper(I) chloride, 12.61 g of copper(II) chloride and 120 ml of acetonitrile dropwise at room temperature, and the mixture was stirred for 3 hours. This reaction solution was poured into a mixture of ice and hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 13.16 g of 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy)-2-(ethoxycarbonyl)methoxypyridine [present compound 7-8].

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d1370be6abbf443c97038a8f7cc52ce5
Source dataset
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06537948B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes