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

HRID 428571Notes

Reaction equation

HRID 428571 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH2:14][NH2:15].C(=O)([O-])O.[K+]>CC(C)=O.O>[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH2:14][NH:15][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=1

Participants

6

Reactant 3

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

Product 1

HCID 10903782N-(2,2-dimethoxyethyl)-4-iodobenzamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent3×HCID 962WaterSolvent

Procedure

A solution of 4-iodobenzoyl chloride (100 g, 375.6 mmol) in 300 mL of acetone was added to a solution of aminoacetaldehyde dimethylacetal (41.4 g, 1.05 equiv.) and potassium hydrogen carbonate (39.5 g, 1.05 equiv.) in 270 mL of acetone and 450 mL of water. After completion of the reaction, acetone was removed under reduced pressure at no more than 35° C. to induce crystallization. The crystal slurry was filtered, washed and dried in vacuo at <50° C., to give 120 g (95 M %, HPLC area % 96) of the title compound.

Workup

  1. customwas removed under reduced pressure at no more than 35° C.
  2. customcrystallization
  3. filtrationThe crystal slurry was filtered
  4. washwashed
  5. customdried in vacuo at <50° C.

Sources & evidence

ORD record
ord-e4b297d7490042c1a06a763fd4851e7e
Source dataset
uspto-grants-2001_11
Patent number
US06313308B1

Reaction notes

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