Réaction #44782

Équation de réaction

4-iodobenzoyl chloride

2-aminoacetaldehyde dimethylacetal

potassium bicarbonate

→

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

Rendement 96.8%

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   AutreThe cooling bath was removed
3. 3
   workup.STIRRINGthe reaction stirred for 3 hours
4. 4
   ConcentrationThe reaction was concentrated
5. 5
   workup.ADDITIONdiluted with water
6. 6
   AutreThe resulting solid was isolated by filtration
7. 7
   Autredried

Mode opératoire

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.

Source