Triethylamine → 2-Chloro-n-(1-methylethyl)-n-propyl-6-(trimethylsilyl)benzamide

HRID 725481Notes

Reaction equation

HRID 725481 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([Si:18]([CH3:21])([CH3:20])[CH3:19])[C:10]=1[C:11](Cl)=[O:12].Cl.[CH2:23]([NH:26][CH:27]([CH3:29])[CH3:28])[CH2:24][CH3:25]>C1(C)C=CC=CC=1>[Cl:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([Si:18]([CH3:21])([CH3:20])[CH3:19])[C:10]=1[C:11]([N:26]([CH:27]([CH3:29])[CH3:28])[CH2:23][CH2:24][CH3:25])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13344554(Propan-2-yl)(propyl)amine hydrochlorideHCID 151835572-Chloro-6-(trimethylsilyl)benzoyl chloride

Product 1

HCID 186303012-Chloro-n-(1-methylethyl)-n-propyl-6-(trimethylsilyl)benzamideYield 80.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethylamine (27.89 mL, 200 mmol) was added to a mixture of the compound of Example b (2.47 g, 10 mmol) and N-propyl-N-iso-propylamine hydrochloride (~92 mmol) in toluene (100 mL). The reaction was stirred overnight at ambient temperature, then was partitioned between ethyl acetate and dilute citric acid. The organic phase was washed with brine, dried (MgSO4), and concentrated to afford 2.50 g of the title compound as a waxy amber solid, an 80% yield.

Workup

  1. customwas partitioned between ethyl acetate and dilute citric acid
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c9587d6b721f4b959ca2015cfb1ea773
Source dataset
uspto-grants-1998_01
Patent number
US05705513

Reaction notes

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