Methyl iodide → 2-Chloro-n-ethyl-6-(ethyldimethylsilyl)benzamide

HRID 356400Notes

Reaction equation

[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Si:13]([CH3:16])([CH3:15])[CH3:14])[C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5].[CH3:17]N(CCN(C)C)C.[Li]C(C)(C)C.CCCCC.CI>C1COCC1>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Si:13]([CH2:15][CH3:17])([CH3:14])[CH3:16])[C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of the compound of example 45 (1.28 g, 5 mmol) and TMEDA (0.91 mL, 6.0 mmol, 1.2 eq) in THF at -78° C. was added a 1.7M solution of t-BuLi in pentane (7.1 mL, 12 mmol, 2.4 eq) such that the temperature was less than -70° C. The reaction was stirred at -78° C. for 2 h and methyl iodide (0.44 mL, 7.0 mmol, 1.4 eq) was added. The reaction was stirred for 15 min at -78° C. and worked up in the usual manner. The crude product was recrystallized from aq methanol and then from hexanes to afford the title compound as white crystals (0.62 g, 46%). m.p. 94°-95° C.

Workup

customwas less than -70° C
stirringThe reaction was stirred for 15 min at -78° C.
customThe crude product was recrystallized from aq methanol

Sources & evidence

ORD record: ord-4ad21b26f4ff4181bc6520c966fed506
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05834447

Reaction notes

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