Acetonitrile → HCID 22557376, compound

HRID 984051Notes

Reaction equation

HRID 984051 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.C[N:7]([CH3:10])CC.C(#N)C.[Cl:14][C:15]1[CH:16]=[C:17]([N:31]2[C:36](=[O:37])[NH:35][C:34](=[O:38])[CH:33]=[N:32]2)[CH:18]=[C:19]([Cl:30])[C:20]=1[C:21](=O)C1C=CC(Cl)=CC=1.[NH4+].[Cl-:40].[CH2:41]1[CH2:45][O:44][CH2:43][CH2:42]1>>[Cl:30][C:19]1[CH:18]=[C:17]([N:31]2[C:36](=[O:37])[NH:35][C:34](=[O:38])[CH:33]=[N:32]2)[CH:16]=[C:15]([Cl:14])[C:20]=1[CH2:21][C:45]([C:41]1[CH:3]=[CH:2][C:1]([Cl:40])=[CH:43][CH:42]=1)([OH:44])[C:10]#[N:7]

Participants

7

Reactant 6

HCID 6342AcetonitrileHCID 8028Tetrahydrofuran2×HCID 11723DimethylethylamineHCID 25517Ammonium ChlorideHCID 156641902-(3,5-Dichloro-4-(4-chlorobenzoyl)phenyl)-1,2,4-triazine-3,5(2H,4H)-dioneHCID 178418339Butyllithium

Product 1

HCID 22557376HCID 22557376, compoundYield 8%

Conditions

Temperature
-20 °C

Procedure

n-Butyllithium (0.1 mol) was added dropwise at −70° C. under N2 flow to a solution of N,N-dimethylethanamine (0.1 mol) in THF (100 ml). The mixture was stirred at −20° C. for 30 minutes and cooled again to −70° C. Acetonitrile (0.1 mol) was added dropwise. The mixture was stirred at −20° C. for 1 hour and cooled again to −70° C. A solution of 2-[3,5-dichloro-4-(4-chlorobenzoyl)phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (0.05 mol) in THF (100 ml) was added dropwise. The mixture was stirred at −70° C. for 1 hour, then poured out into NH4Cl 10% and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2). Two pure fractions were collected and their solvents were evaporated, yielding 1.62 g (8%) of (±)-2,6-dichloro-α-(4-chlorophenyl)-4-[4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl]-α-hydroxybenzenepropanenitrile (compound 122).

Workup

  1. temperaturecooled again to −70° C
  2. stirringThe mixture was stirred at −20° C. for 1 hour
  3. temperaturecooled again to −70° C
  4. stirringThe mixture was stirred at −70° C. for 1 hour
  5. extractionextracted with EtOAc
  6. customThe organic layer was separated
  7. customdried
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2)
  11. customTwo pure fractions were collected
  12. customtheir solvents were evaporated

Sources & evidence

ORD record
ord-cf2a32516391481abb8f4cf104053444
Source dataset
uspto-grants-2005_03
Patent number
US06867207B2

Reaction notes

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