4-Iodobenzoyl chloride → N-(2,2-dimethoxyethyl)-4-iodobenzamide

HRID 16504

Reaktionsgleichung

Reaktionsgleichung von HRID 16504
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].C(=O)(O)[O-].[K+].[I:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>CC(C)=O>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH:5][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([I:13])=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 743734-Iodobenzoyl chlorideHCID 89728Aminoacetaldehyde dimethyl acetalHCID 516893Potassium Bicarbonate

Produkt 1

HCID 10903782N-(2,2-dimethoxyethyl)-4-iodobenzamideAusbeute 96,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of 2-aminoacetaldehyde dimethylacetal (12.3 mL, 112 mmol) in a mixture of acetone (50 mL) and aqueous potassium bicarbonate (12 g, 122 mmol in 110 mL of water) was stirred and cooled to −5° C., as a solution of 4-iodobenzoyl chloride (25 g, 94 mmol) was added dropwise. The cooling bath was removed and the reaction stirred for 3 hours. The reaction was concentrated and diluted with water. The resulting solid was isolated by filtration and dried to give 30.5 g of N-(2,2-dimethoxyethyl)-4-iodobenzamide, 1H NMR (400 MHz, CDCl3) δ 7.78 (d, 2H), 7.46 (d, 2H), 6.34 (s, 1H), 4.44 (t, 1H), 3.58 (t, 2H), 3.42 (s, 6H) ppm.

Aufarbeitung

  1. additionwas added dropwise
  2. customThe cooling bath was removed
  3. stirringthe reaction stirred for 3 hours
  4. concentrationThe reaction was concentrated
  5. additiondiluted with water
  6. customThe resulting solid was isolated by filtration
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c8f62c16fc7643aa956289fccab212d7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737145B2

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