Hexachloroethane → HCID 18630045, compound

HRID 1440571Notes

Reaction equation

HRID 1440571 reaction equation
[Li]C(CC)C.C1CCCCC1.[CH2:12]([NH:14][C:15]([C:17]1[CH:21]=[CH:20][S:19][CH:18]=1)=[O:16])[CH3:13].CN(CCN(C)C)C.[Cl:30]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[CH2:12]([NH:14][C:15]([C:17]1[CH:21]=[CH:20][S:19][C:18]=1[Cl:30])=[O:16])[CH3:13]

Participants

7

Reactant 5

HCID 6214HexachloroethaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078CyclohexaneHCID 154523283-Thiophenecarboxamide,N-ethyl-HCID 178418400CID 53628100

Product 1

HCID 18630045HCID 18630045, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 1.3M s-BuLi in cyclohexane (44 mL, 57.2 mmol) was added dropwise to a -78° C. cooled solution of N-ethyl-3-thiophenecarboxamide (4.04 g, 26 mmol) and TMEDA (6.65 g, 57.2 mmol) in THF (100 mL). After stirring for 30 min at -78° C., a solution of hexachloroethane (13.54 g, 57.2 mmol) in THF (20 mL) was added dropwise. The resulting reaction mixture was warmed to RT over 1 h, quenched with dilute aq citric acid, and extracted with EtOAc (3×). The combined organic extracts were dried (MgSO4), concentrated, and purified by HPLC with 3:7 EtOAc/hexanes to give 2.8 g of N-ethyl-2-chloro-3-thiophenecarboxamide as a yellow oil, a 57% yield.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas warmed to RT over 1 h
  3. customquenched with dilute aq citric acid
  4. extractionextracted with EtOAc (3×)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by HPLC with 3:7 EtOAc/hexanes

Sources & evidence

ORD record
ord-788aaf4095d147ef9d3e20c0f097ba77
Source dataset
uspto-grants-1996_03
Patent number
US05498630

Reaction notes

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