Hydrochloric Acid → ([2-(2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy)phenoxy]methyl)benzene

HRID 1241281Notes

Reaction equation

HRID 1241281 reaction equation
N(OCCC(C)C)=O.[CH2:9]([O:16][C:17]1[CH:44]=[CH:43][CH:42]=[CH:41][C:18]=1[O:19][C:20]1[CH:26]=[C:25]([N:27]2[C:32](=[O:33])[CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[N:29]([CH3:38])[C:28]2=[O:39])[C:24]([F:40])=[CH:23][C:21]=1N)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[ClH:45]>[Cu]Cl.[Cu](Cl)Cl.C(#N)C>[Cl:45][C:21]1[CH:23]=[C:24]([F:40])[C:25]([N:27]2[C:32](=[O:33])[CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[N:29]([CH3:38])[C:28]2=[O:39])=[CH:26][C:20]=1[O:19][C:18]1[CH:41]=[CH:42][CH:43]=[CH:44][C:17]=1[O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 219335252-(2-Benzyloxyphenoxy)-5-fluoro4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]aniline

Product 1

HCID 21933546([2-(2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy)phenoxy]methyl)benzene

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

First, 4.46 g of isoamyl nitrite was added dropwise to a mixture of 6.46 g of 2-(2-benzyloxyphenoxy)-5-fluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]aniline, 2.45 g of copper(I) chloride, 5.04 g of copper(II) chloride, and 90 ml of acetonitrile at room temperature, and the mixture was stirred for 1 hour. The reaction mixture was poured into 2% hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 4.6 g of ([2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}phenoxy]methyl)benzene.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a6c2426e2aed4cca9e28d037df574846
Source dataset
uspto-grants-2006_10
Patent number
US07115544B2

Reaction notes

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