Hydrochloric Acid → HCID 18759309, compound

HRID 433710Notes

Reaction equation

HRID 433710 reaction equation
N(OCCC(C)C)=O.[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([CH:42]=[CH:43][CH:44]=1)[O:20][C:21]1[CH:27]=[C:26]([N:28]2[C:33](=[O:34])[CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[N:30]([CH3:39])[C:29]2=[O:40])[C:25]([F:41])=[CH:24][C:22]=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:22]1[CH:24]=[C:25]([F:41])[C:26]([N:28]2[C:33](=[O:34])[CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[N:30]([CH3:39])[C:29]2=[O:40])=[CH:27][C:21]=1[O:20][C:19]1[CH:18]=[C:17]([CH:44]=[CH:43][CH:42]=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 18759314HCID 18759314, compound

Product 1

HCID 18759309HCID 18759309, compound

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

0.34 g of isoamyl nitrite was added dropwise to a mixture of 1.5 g of 2-(3-benzyloxyphenoxy)-5-fluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]aniline, 0.57 g of copper (I) chloride, 1.17 g of copper (II) chloride, and 21 ml of acetonitrile at room temperature, and the mixture was stirred for 1 hour. This reaction solution was poured into 2% 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 1.01 g of ([3-{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. 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-cacceeaa51f4487f857ce90bfbe71bec
Source dataset
uspto-grants-2003_12
Patent number
US06667413B2

Reaction notes

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