Solid Phase Synthesis of N-2-Chlorobenzylbenzamide and Its Crystal Structure

Abstract

Abstract: The title compound was prepared by solid phase synthesis technique. Polystyryl sulfonyl chloride resin 1 was treated with 2-chlorobenzylamine in the presence of pyridine to yield polymer-supported N-2-chlorobenzyl sulfonamide 2. Resin 2 was acylated with benzoyl chloride catalyzed by pyridine to give N-2-chlorobenzyl-N-benzoyl sulfonamide resin 3. After the cleavage of resin 3 using TiCl₄/Zn/THF in a radical way, N-2-chlorobenzylbenzamide(4) was obtained in 92% overall yield. The crystal structure of N-2-chlorobenzylbenzamide was reported as follows: N-2-chlorobenzylbenzamide crystallizes in the monoclinic space group P2₁ with cell parameters: a=0.714 9(3)_nm, b=0.877 2(4)_nm, c=0.970 4(4)_nm; β=95.172(7)°. N-2-Chlorobenzylbenzamide has two kinds of intermolecular hydrogen bonds in the crystal.

Key words: Solid phase organic synthesis, N-2-Chlorobenzylbenzamide, Crystal structure

CLC Number:

O621.15

TrendMD:

LUO Jun-Tao, HUANG Wen-Qiang . Solid Phase Synthesis of N-2-Chlorobenzylbenzamide and Its Crystal Structure[J]. Chem. J. Chinese Universities, 2004, 25(1): 56.

References

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