Hexachloroethane → HCID 22721725, compound

HRID 396583Notes

Reaction equation

HRID 396583 reaction equation
ClC(Cl)(Cl)C(Cl)(Cl)Cl.[CH:9]([CH:11]([NH:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)=[O:18])[CH2:12][CH:13]([CH3:15])[CH3:14])=O.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC#N.[Cl-].[Na+].O>[CH2:12]([C:11]1[N:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[O:18][CH:9]=1)[CH:13]([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 17917748HCID 17917748, compound

Product 1

HCID 22721725HCID 22721725, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Hexachloroethane (445 mg, 1.87 mmol) was dissolved in 5 mL CH3CN. A solution of pyridine-2-carboxylic acid (1-formyl-3-methylbutyl)amide (137.5 mg, 0.625 mmol) in 2 mL CH3CN was added followed by triethylamine (375 mg, 3.75 mmol) and triphenylphosphine (491 mg, 1.87 mmol). The resulting mixture was stirred for ½ h, poured into brine, and extracted with 2×25 mL EtOAc. The combined extracts were washed with 1×50 mL brine, dried with Na2SO4 and evaporated to 665 mg of a tan solid which was flash chromatographed through SiO2 (20%-35% hexane/EtOAc) yielding 100 mg (76%) of the title compound as an amber oil, MS (ES) 203 (M+).

Workup

  1. extractionextracted with 2×25 mL EtOAc
  2. washThe combined extracts were washed with 1×50 mL brine
  3. dry with materialdried with Na2SO4
  4. customevaporated to 665 mg of a tan solid which
  5. customchromatographed through SiO2 (20%-35% hexane/EtOAc)

Sources & evidence

ORD record
ord-33da552a2fe948d6875cadaecc3e5623
Source dataset
uspto-grants-2003_08
Patent number
US06608057B2

Reaction notes

Loading…