Triethylamine → Ethyl 2-[4-(3-isopropyl-4-methoxybenzyl)-3,5-dimethylanilino]-2-oxoacetate

HRID 392892Notes

Reaction equation

HRID 392892 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:7][C:8]1[C:14]([CH3:15])=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=1[CH3:16])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:29](Cl)([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:30]>ClCCl>[CH:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:7][C:8]1[C:9]([CH3:16])=[CH:10][C:11]([NH:12][C:29](=[O:30])[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:13][C:14]=1[CH3:15])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 112890854-(3-Isopropyl-4-methoxybenzyl)-3,5-dimethylaniline

Product 1

HCID 10110509Ethyl 2-[4-(3-isopropyl-4-methoxybenzyl)-3,5-dimethylanilino]-2-oxoacetateYield 38.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

246 mg (0.86 mmol) of 4-(3-isopropyl-4-methoxybenzyl)-3,5-dimethylaniline (Example VII) are dissolved with 97 mg (0.96 mmol) of triethylamine in 10 ml of dichloromethane, and 160 mg (1.17 mmol) of ethoxalyl chloride are added dropwise. The mixture is stirred at room temperature for 4 hours, washed with sodium bicarbonate solution and water and dried over sodium sulphate, and the solvent is removed in vacuo. Purification by chromatography affords 128 mg (38%) of ethyl 2-[4-(3-isopropyl-4-methoxybenzyl)-3,5-dimethylanilino]-2-oxoacetate.

Workup

  1. additionare added dropwise
  2. washwashed with sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is removed in vacuo
  5. customPurification by chromatography

Sources & evidence

ORD record
ord-19324026a4f0434ebeee230cd523f0d6
Source dataset
uspto-grants-2004_10
Patent number
US06803480B2

Reaction notes

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