Reaction #1885017

Reaction equation

water

4-iodobenzoyl chloride

2-aminophenol

triethylamine

→

powdery white solid

Yield 97.0%

4-iodo-N-(2-hydroxyphenyl)benzamide

Yield 97.0%

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   OtherIn a 300 mL three-neck flask were put
2. 2
   workup.ADDITIONwas dropped
3. 3
   workup.STIRRINGThe solution was stirred at 0° C. for 5 hours under a nitrogen stream
4. 4
   Extractionan aqueous layer of the obtained mixture was extracted with ethyl acetate
5. 5
   ExtractionAfter the extraction
6. 6
   Washwashed with 1 M hydrochloric acid
7. 7
   workup.ADDITIONAfter the washing, magnesium sulfate was added into the organic layer
8. 8
   Otherto dry the organic layer
9. 9
   FiltrationAfter the drying, the mixture was subjected to suction filtration through Celite (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855)
10. 10
    Otherto give a filtrate
11. 11
    OtherThe solid, which was obtained by condensation of the obtained filtrate
12. 12
    Otherwas recrystallized with a mixed solvent of ethyl acetate and hexane

Procedure

In a 300 mL three-neck flask were put 10 g (92 mmol) of 2-aminophenol and 7.0 mL of triethylamine and was added 100 mL of tetrahydrofuran (THF). The solution was stirred at 0° C. for 20 minutes. After the stirring, a solution in which 0.10 mol of 4-iodobenzoyl chloride was dissolved in 100 mL of tetrahydrofuran (THF) was dropped. The solution was stirred at 0° C. for 5 hours under a nitrogen stream. After the stirring, the solution was added to about 300 mL of water and an aqueous layer of the obtained mixture was extracted with ethyl acetate. After the extraction, the extracted solution was combined with the organic layer and washed with 1 M hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate and brine in this order. After the washing, magnesium sulfate was added into the organic layer to dry the organic layer. After the drying, the mixture was subjected to suction filtration through Celite (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855) to give a filtrate. The solid, which was obtained by condensation of the obtained filtrate, was recrystallized with a mixed solvent of ethyl acetate and hexane to give 30 g of a powdery white solid in a yield of 97%.

Source