Hydrochloric Acid → HCID 18759301, compound

HRID 433706Notes

Reaction equation

HRID 433706 reaction equation
N(OCCC(C)C)=O.[CH2:9]([O:16][C:17]1[CH:44]=[CH:43][C:20]([O:21][C:22]2[CH:28]=[C:27]([N:29]3[C:34](=[O:35])[CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[N:31]([CH3:40])[C:30]3=[O:41])[C:26]([F:42])=[CH:25][C:23]=2N)=[CH:19][CH:18]=1)[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:23]1[CH:25]=[C:26]([F:42])[C:27]([N:29]2[C:34](=[O:35])[CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[N:31]([CH3:40])[C:30]2=[O:41])=[CH:28][C:22]=1[O:21][C:20]1[CH:43]=[CH:44][C:17]([O:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 18759312HCID 18759312, compound

Product 1

HCID 18759301HCID 18759301, compound

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

0.46 g of isoamyl nitrite was added dropwise to a mixture of 1.0 g of 2-(4-benzyloxyphenoxy)-5-fluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]aniline, 0.38 g of copper (I) chloride, 0.78 g of copper (II) chloride, and 14 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 0.73 g of ([4-{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-24e506f234d046df93fe7a62d939517b
Source dataset
uspto-grants-2003_12
Patent number
US06667413B2

Reaction notes

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