2-(4-Chlorophenyl)-2-oxoethyl thiocyanate → [4-(4-Chloro-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

HRID 604875

反応式

HRID 604875 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:15])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=O)[CH2:24][S:25][C:26]#[N:27])=[CH:19][CH:18]=1>C(O)C.O1CCOCC1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:27]=[C:26]([NH:15][C:5]3[CH:6]=[CH:7][C:8]([N:9]4[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]4)=[C:3]([O:2][CH3:1])[CH:4]=3)[S:25][CH:24]=2)=[CH:19][CH:18]=1

参加物

5

反応物 2

HCID 880132-(4-Chlorophenyl)-2-oxoethyl thiocyanateHCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline

生成物 1

HCID 86624674[4-(4-Chloro-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 51 mg (0.25 mmol) 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine and of 53 mg (0.25 mmol) 1-(4-chloro-phenyl)-2-thiocyanato-ethanone in ethanol (1.25 ml) and dioxane (1.25 ml) was refluxed over night. After cooling to room temperature the solvent was evaporated under vacuo and the residue was purified on silica gel with methylene chloride/methanol 19/1 yielding 35 mg (35%) [4-(4-chloro-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a yellow solid. MS ISP (m/e): 397.1/399.1 (100/50) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.54 (s, 1H), 7.96 (d, 2H), 7.86 (s, 1H), 7.68 (s, 1H), 7.50 (d, 2H), 7.48 (s, 1H), 7.31 (d, 1H), 7.22 (d, 1H), 7.06 (s, 1H).

後処理

  1. customwas evaporated under vacuo
  2. customthe residue was purified on silica gel with methylene chloride/methanol 19/1 yielding 35 mg (35%) [4-(4-chloro-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a yellow solid

出典と根拠

ORDレコード
ord-ff47168e96584356b0921843bccb64bb
出典データセット
uspto-grants-2011_03
特許番号
US07910740B2

関連ノート

読み込み中…