Hexachloroethane → HCID 18630338, compound

HRID 1070278Notes

Reaction equation

HRID 1070278 reaction equation
[Li]C(CC)C.C1CCCCC1.[C:12]([C:16]1[CH:26]=[CH:25][C:19]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].CN(CCN(C)C)C.[Cl:35]C(Cl)(Cl)C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:35][C:18]1[CH:17]=[C:16]([C:12]([CH3:13])([CH3:15])[CH3:14])[CH:26]=[CH:25][C:19]=1[C:20]([NH:22][CH2:23][CH3:24])=[O:21]

Participants

8

Reactant 6

HCID 6214HexachloroethaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078CyclohexaneHCID 516892Sodium BicarbonateHCID 4300248HCID 4300248, compoundHCID 178418400CID 53628100

Product 1

HCID 18630338HCID 18630338, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

1.3 M s-BuLi in cyclohexane (41 mL, 0.053 mol) was added dropwise to a solution of the above amide (5 g, 0.024 mol) and TMEDA (4 ml, 0.027 mol) in THF, cooled to −78° C. under nitrogen. After 30 min a solution of hexachloroethane (6.4 g, 0.027 mol) in THF was added. After 0.5 h at −78° C. the reaction mixture was warmed to −30° C. and poured into dilute aq NaHCO3 and extracted with ether. The ether extract was washed with water and brine, dried (MgSO4) and concentrated. The resulting solid was recrystallized from cyclohexane to give 5 g of 2-chloro-4-t-butyl-N-ethylbenzamide, a white solid.

Workup

  1. temperatureAfter 0.5 h at −78° C. the reaction mixture was warmed to −30° C.
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washwas washed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe resulting solid was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-65434e3acd1e42b2afa17b898938efaa
Source dataset
uspto-grants-2001_06
Patent number
US06252078B1

Reaction notes

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