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 language | English (US) |
|---|---|
| Pages (from-to) | 320-323 |
| Number of pages | 4 |
| Journal | Jiegou Huaxue |
| Volume | 23 |
| Issue number | 3 |
| State | Published - 2004 |
| Externally published | Yes |
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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 journal › Article
}
TY - JOUR
T1 - Solid phase synthesis of N-p-methylbenzyl benzamide and its crystal structure
AU - Luo, Jun Tao
AU - Huang, Wen Qiang
PY - 2004
Y1 - 2004
N2 - 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.
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.
KW - Crystal structure
KW - N-p-methylbenzyl benzamide
KW - Solid phase organic synthesis
UR - http://www.scopus.com/inward/record.url?scp=4644228018&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=4644228018&partnerID=8YFLogxK
M3 - Article
VL - 23
SP - 320
EP - 323
JO - Jiegou Huaxue
JF - Jiegou Huaxue
SN - 0254-5861
IS - 3
ER -