Water → 2-(2,6-Dichloro-4-nitro-phenyl)-2-methyl-propionitrile

HRID 1072485Notes

Reaction equation

HRID 1072485 reaction equation
BrCCCCCCCCCCCCCCC.[Cl:17][C:18]1[CH:23]=[C:22]([N:24]2C(=O)NC(=O)C=N2)[CH:21]=[C:20](Cl)[C:19]=1[C:33]([C:36]1SC(CC(O)=O)=C(C2C=CC=CC=2)[N:40]=1)([CH3:35])[CH3:34].C([O-])(O)=[O:52].[Na+].[Na+].[Cl-:57].[OH2:58]>CN(C=O)C>[Cl:57][C:20]1[CH:21]=[C:22]([N+:24]([O-:52])=[O:58])[CH:23]=[C:18]([Cl:17])[C:19]=1[C:33]([CH3:35])([CH3:34])[C:36]#[N:40]

Participants

7

Reactant 5

HCID 962WaterHCID 5234Sodium ChlorideHCID 123941-BromopentadecaneHCID 516892Sodium BicarbonateHCID 158708342-[1-[2,6-dichloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)yl)phenyl]-1-methylethyl]-4-phenyl-5-thiazoleacetic acid

Product 1

HCID 113459512-(2,6-Dichloro-4-nitro-phenyl)-2-methyl-propionitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of 1-bromopentadecane (0.0051 mole) in DMF (18 ml) was added dropwise at room temperature to a mixture of intermediate (10) (0.00483 mole) and NaHCO3 (0.0051 mole) in DMF (10 ml). The mixture was stirred at 70° C. for 5 hours and at 45° C. overnight, then brought to room temperature. H2O and NaCl were added. The mixture was extracted with EtOAc. The organic layer was separated, washed with a saturated NaCl solution, dried (MgSO4), filtered and the solvent was evaporated. The residue (3.8 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2; 15-40 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.49 g of compound 2 having a melting point of 80° C. and represented by the formula

Workup

  1. custombrought to room temperature
  2. extractionThe mixture was extracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with a saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue (3.8 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2; 15-40 μm)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-639beb1d10334682946c243a0cfee31c
Source dataset
uspto-grants-2005_06
Patent number
US06911444B2

Reaction notes

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