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

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Chloride	HCID 5234	—
Reactant	1-Bromopentadecane	HCID 12394	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	2-[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	HCID 15870834	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(2,6-Dichloro-4-nitro-phenyl)-2-methyl-propionitrile	HCID 11345951	—

Reaction Conditions

Temperature	45 °C

Reaction Steps

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

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06911444B2
Source dataset	uspto-grants-2005_06
ORD ID	ord-639beb1d10334682946c243a0cfee31c
Source note	uspto-grants-2005_06