Triethylamine → HCID 2524544, compound

HRID 247833Notes

Reaction equation

HRID 247833 reaction equation
[C:1]([O:4][CH2:5][C:6](Cl)=[O:7])(=[O:3])[CH3:2].[CH:9]([C:12]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[C:13]=1[NH2:14])([CH3:11])[CH3:10].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:21][CH:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:12]([CH:9]([CH3:11])[CH3:10])[C:13]=1[NH:14][C:6](=[O:7])[CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 32484Diisopropylaniline

Product 1

HCID 2524544HCID 2524544, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of acetoxyacetyl chloride (13.5 g, 98.7 mmol) in toluene (70 mL) at 0° C. is added dropwise via a dropping funnel a solution of 2,6-diisopropylaniline (17.5 g, 98.7 mmol) and triethylamine (20.6 mL, 148.1 mmol) in toluene (20 mL). After completion of the addition, the mixture is allowed to warm to room temperature and stirred for 24 hours. The mixture is filtered through a small pad of silica gel. The filtrate is concentrated to afford 11 g of a brown solid. The precipitate is suspended in ethyl acetate and stirred overnight. After filtration, the filtrate is concentrated to give another 10 g of a brown solid. Recrystallization (ethyl acetate/hexane) of the combined material provided 12 g of the title compound as an off-white solid; mp 179°-182° C.

Workup

  1. additionAfter completion of the addition
  2. filtrationThe mixture is filtered through a small pad of silica gel
  3. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-ce59a00d2fe9408abc0e7294a91e20fd
Source dataset
uspto-grants-1993_05
Patent number
US05208224

Reaction notes

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