Toluene → 4-[(5S,9R)-7-Benzyl-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-9-yl]-benzonitrile

HRID 456720

反応式

[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])/[C:12](=[CH:15]\[C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)/[N:11]([CH3:24])[C:10]2=[O:25])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH2:26]1N2CN3CN(C2)[CH2:28][N:27]1[CH2:34]3.C(NCC(O)=O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C1(C)C=CC=CC=1>CN1CCCC1=O>[CH2:26]([N:27]1[CH2:34][C@@H:15]([C:16]2[CH:17]=[CH:18][C:19]([C:20]#[N:21])=[CH:22][CH:23]=2)[C@:12]2([N:11]([CH3:24])[C:10](=[O:25])[N:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)[C:13]2=[O:14])[CH2:28]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

参加物

反応条件

温度: 140 °C

実験手順

A mixture of (E)-4-((1-(3,5-dichlorophenyl)-3-methyl-2,5-dioxoimidazolidin-4-ylidene)methyl)benzonitrile (1.05 g, 2.82 mmol), hexamethylenetetramine (0.395 g, 2.82 mmol), N-benzylglycine (1.17 g, 7.05 mmol), toluene (5 ml), and 1-methyl-2-pyrrolidinone (NMP, 10 ml) was heated to 140° C. The extent of reaction was monitored by HPLC. After 72 hours, the reaction had stopped short of completion. The ratio of product to starting material ((E)-4-((1-(3,5-dichlorophenyl)-3-methyl-2,5-dioxoimidazolidin-4-ylidene)methyl)benzonitrile) was 1.36:1. Mass spectra of the mixture indicated the presence of the desired product. The mixture was washed with water and extracted into toluene. The impure product was obtained as an oil. Comparison of the product obtained to authentic material was made by HPLC. The ratio of the desired (5S, 9R) isomer to the undesired was 19:1.

後処理

customThe extent of reaction

出典と根拠

ORDレコード: ord-2d6bc040ace94bfc83405eb1ce3346cd
出典データセット: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07186727B2

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

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