Chlorotrimethylsilane → HCID 18630136, compound

HRID 1458096Notes

Reaction equation

HRID 1458096 reaction equation
[Li]C(CC)C.C1CCCCC1.[CH2:12]([NH:14][C:15]([C:17]1[CH:21]=[CH:20][S:19][C:18]=1[Cl:22])=[O:16])[CH3:13].CN(CCN(C)C)C.[CH3:31][Si:32](Cl)([CH3:34])[CH3:33]>C1COCC1.CCOCC>[Cl:22][C:18]1[S:19][CH:20]=[C:21]([Si:32]([CH3:34])([CH3:33])[CH3:31])[C:17]=1[C:15]([NH:14][CH2:12][CH3:13])=[O:16]

Participants

8

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078CyclohexaneHCID 18630045HCID 18630045, compoundHCID 178418400CID 53628100

Product 1

HCID 18630136HCID 18630136, compoundYield 11.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-100 °C

Procedure

A solution of 1.3M s-BuLi in cyclohexane (16.15 mL, 21 mmol) was added dropwise to an ether/liquid N2 cooled (-100° C.) solution of N-ethyl-2-chloro-3-thiophenecarboxamide (1.90 g, 10 mmol) and TMEDA (3.17 L, 21 mmol) in THF (100 mL). After stirring for 30 min at -100° C., TMSCl (2.28 g, 21 mmol) was added in a single portion. The resulting reaction mixture was warmed to -25° C. 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 3:17 EtOAc/hexanes to afford 0.3 g of the title compound as a white solid, an 11% yield. m.p. 46°-48° C.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas warmed to -25° C. 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 3:17 EtOAc/hexanes

Sources & evidence

ORD record
ord-5865deb653664320912dba6dc573640d
Source dataset
uspto-grants-1998_12
Patent number
US05849723

Reaction notes

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