Hexachloroethane → HCID 54330115, compound
Reaction equation
[Li]C(CC)C.C1CCCCC1.C(=O)=O.CC(C)=O.CN(CCN(C)C)C.[CH2:27]([N:29]([CH3:44])[C:30](=[O:43])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[N:37]([CH3:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[CH3:28].[Cl:45]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.O>[Cl:45][C:36]1[CH:35]=[CH:34][CH:33]=[C:32]([N:37]([C:38]([CH3:39])([CH3:40])[CH3:41])[CH3:42])[C:31]=1[C:30]([N:29]([CH2:27][CH3:28])[CH3:44])=[O:43]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -30 °C
Procedure
A solution of 1.3M s-BuLi in cyclohexane (3.7 mL, 4.8 mmol) was added dropwise to a dry-ice/acetone cooled solution of TMEDA (0.7 mL, 4.8 mmol) in THF (10 mL), followed by the dropwise addition of a solution of N-ethyl-N-methyl 2-(N-methyl-N-tert-butylamino)benzamide (1.0 g, 4.0 mmol) in THF (5 mL). The reaction mixture was briefly warmed to -30° C., then cooled to -78° C. and stirred for 15 min. A solution of hexachloroethane (2.8 g, 12.1 mmol) in THF (5 mL) was added. This mixture was stirred for 1 h at -78° C., then was warmed to -30° C., diluted with water, and extracted with EtOAc (2×). The combined organic extracts were dried (MgSO4), concentrated, and purified by HPLC with 1:4 EtOAc/cyclohexane to give 528 mg of the title compound as a yellow oil, a 46% yield.
Workup
- temperaturecooled to -78° C.
- stirringThis mixture was stirred for 1 h at -78° C.
- temperaturewas warmed to -30° C.
- extractionextracted with EtOAc (2×)
- dry with materialThe combined organic extracts were dried (MgSO4)
- concentrationconcentrated
- custompurified by HPLC with 1:4 EtOAc/cyclohexane
Sources & evidence
- ORD record
- ord-6c99230d5df44970a176762374295884
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05849723
Reaction notes
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