Acetyl chloride → n-Acetyl-2-chloro-n-ethyl-6-(trimethylsilyl)benzamide

HRID 356350Notes

Reaction equation

HRID 356350 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:11][C:12]1[CH:22]=[CH:21][CH:20]=[C:19]([Si:23]([CH3:26])([CH3:25])[CH3:24])[C:13]=1[C:14]([NH:16][CH2:17][CH3:18])=[O:15].[C:27](Cl)(=O)[CH3:28].C1C[O:34]CC1>>[C:17]([N:16]([CH2:27][CH3:28])[C:14](=[O:15])[C:13]1[C:19]([Si:23]([CH3:25])([CH3:24])[CH3:26])=[CH:20][CH:21]=[CH:22][C:12]=1[Cl:11])(=[O:34])[CH3:18]

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 8028Tetrahydrofuran3×HCID 2724254Sodium bis(trimethylsilyl)amideHCID 186303792-Chloro-n-ethyl-6-(trimethylsilyl)benzamide

Product 1

HCID 18630333n-Acetyl-2-chloro-n-ethyl-6-(trimethylsilyl)benzamideYield 17%

Procedure

1M sodium bis(trimethylsilyl)amide in THF (5.5 mL, 5.5 mmol) was added dropwise over several min to a solution of the compound of Example 45 (1.28 g, 5 mmol) in THF (30 mL). The resulting mixture was cooled with a water bath while a solution of acetyl chloride (0.432 g, 5.5 mmol) in THF (10 mL) was added, maintaining the internal reaction temperature ~ 25° C. After 1 h, the resulting reaction mixture was partitioned between sat aq NaHCO3 and ether. The ether phase was dried (MgSO4), concentrated, and purified by RC with 1:4 ethyl acetate/hexanes to afford 0.25 g of the title compound as a pale yellow oil, a 17% yield.

Workup

  1. additionwas added
  2. temperaturemaintaining the internal reaction temperature ~ 25° C
  3. customthe resulting reaction mixture
  4. customwas partitioned
  5. dry with materialThe ether phase was dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by RC with 1:4 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4cef13ecbfdb4476a69ccae32bce5f87
Source dataset
uspto-grants-1998_11
Patent number
US05834447

Reaction notes

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