Solid phase synthesis of N-p-methylbenzyl benzamide and its crystal structure

Jun Tao Luo, Wen Qiang Huang

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

N-p-Methylbenzyl benzamide 4 was synthesized by means of solid phase synthesis technique. Polystyryl-sulfonyl chloride resin 1 was treated with p-methylbenzyl amine in the presence of pyridine to yield polymer-supported N-p-methylbenzyl sulfonamide 2. After acylation of resin 2 with benzoyl chloride, N-p-methylbenzyl-N-benzoyl sulfonamide resin 3 was obtained. Resin 3 was cleaved with TiCl4/Zn/THF in radical way to offer 4 in 76% yield. The crystal structure of 4 was determined by single-crystal X-ray diffraction with the following data: orthorhombic, space group Pna21, a = 0.9549(6), b = 1.1169(7), c = 1.1774(7) nm, C15H15ON, Mr = 225.28, V = 1.2557(13) nm3, Z = 4, Dc = 1.192 g/cm3, μ = 0.075 mm-1, F(000) = 480, S = 0.912, the final R = 0.0478 and wR = 0.1013. There exist intermolecular hydrogen bonds in the N-p-methylbenzyl benzamide crystal.

Original languageEnglish (US)
Pages (from-to)320-323
Number of pages4
JournalJiegou Huaxue
Volume23
Issue number3
StatePublished - 2004
Externally publishedYes

Fingerprint

resins
solid phases
Resins
Crystal structure
crystal structure
Sulfonamides
synthesis
chlorides
acylation
Acylation
Amines
pyridines
Hydrogen bonds
amines
Polymers
Single crystals
hydrogen bonds
X ray diffraction
Crystals
benzamide

Keywords

  • Crystal structure
  • N-p-methylbenzyl benzamide
  • Solid phase organic synthesis

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Condensed Matter Physics

Cite this

Solid phase synthesis of N-p-methylbenzyl benzamide and its crystal structure. / Luo, Jun Tao; Huang, Wen Qiang.

In: Jiegou Huaxue, Vol. 23, No. 3, 2004, p. 320-323.

Research output: Contribution to journalArticle

Luo, JT & Huang, WQ 2004, 'Solid phase synthesis of N-p-methylbenzyl benzamide and its crystal structure', Jiegou Huaxue, vol. 23, no. 3, pp. 320-323.
Luo, Jun Tao ; Huang, Wen Qiang. / Solid phase synthesis of N-p-methylbenzyl benzamide and its crystal structure. In: Jiegou Huaxue. 2004 ; Vol. 23, No. 3. pp. 320-323.
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AB - N-p-Methylbenzyl benzamide 4 was synthesized by means of solid phase synthesis technique. Polystyryl-sulfonyl chloride resin 1 was treated with p-methylbenzyl amine in the presence of pyridine to yield polymer-supported N-p-methylbenzyl sulfonamide 2. After acylation of resin 2 with benzoyl chloride, N-p-methylbenzyl-N-benzoyl sulfonamide resin 3 was obtained. Resin 3 was cleaved with TiCl4/Zn/THF in radical way to offer 4 in 76% yield. The crystal structure of 4 was determined by single-crystal X-ray diffraction with the following data: orthorhombic, space group Pna21, a = 0.9549(6), b = 1.1169(7), c = 1.1774(7) nm, C15H15ON, Mr = 225.28, V = 1.2557(13) nm3, Z = 4, Dc = 1.192 g/cm3, μ = 0.075 mm-1, F(000) = 480, S = 0.912, the final R = 0.0478 and wR = 0.1013. There exist intermolecular hydrogen bonds in the N-p-methylbenzyl benzamide crystal.

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