4-Toluenesulfonyl chloride → N-(7-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]naphthalen-1-yl)-4-methylbenzenesulfonamide

HRID 412360ノート

反応式

HRID 412360 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([O:12][C:13]1[CH:14]=[CH:15][C:16]3[N:20]=[C:19]([CH2:21][O:22][C:23]4[CH:36]=[CH:35][C:26]([CH2:27][CH:28]5[S:32][C:31](=[O:33])[NH:30][C:29]5=[O:34])=[CH:25][CH:24]=4)[N:18]([CH3:37])[C:17]=3[CH:38]=1)[CH:8]=[CH:7]2.[C:39]1([CH3:49])[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1.C(N(CC)CC)C>O1CCCC1>[O:33]=[C:31]1[NH:30][C:29](=[O:34])[CH:28]([CH2:27][C:26]2[CH:25]=[CH:24][C:23]([O:22][CH2:21][C:19]3[N:18]([CH3:37])[C:17]4[CH:38]=[C:13]([O:12][C:9]5[CH:10]=[C:11]6[C:6]([CH:5]=[CH:4][CH:3]=[C:2]6[NH:1][S:45]([C:42]6[CH:43]=[CH:44][C:39]([CH3:49])=[CH:40][CH:41]=6)(=[O:47])=[O:46])=[CH:7][CH:8]=5)[CH:14]=[CH:15][C:16]=4[N:20]=3)=[CH:36][CH:35]=2)[S:32]1

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 98327115-[4-[6-(8-aminonaphthalen-2-yloxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione

生成物 1

HCID 18537695N-(7-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]naphthalen-1-yl)-4-methylbenzenesulfonamide収率 27%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A mixture of 5-[4-[6-(8-aminonaphthalen-2-yloxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione (0.4 g), p-toluenesulfonyl chloride (0.30 g), triethylamine (0.16 g) and anhydrous tetrahydrofuran (8 ml) was stirred at 50° C. for 5 hours and then at 70° C. for 2 hours. The reaction mixture was concentrated. To the residue was added water and the precipitate was washed with water and tetrahydrofuran to afford the title compound (0.14 g, mp 137-144° C.).

後処理

  1. waitat 70° C. for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionTo the residue was added water
  4. washthe precipitate was washed with water and tetrahydrofuran

出典と根拠

ORDレコード
ord-7bd8e515e1ed4f0b9e6f35b458e77261
出典データセット
uspto-grants-2003_05
特許番号
US06562849B1

反応ノート

読み込み中…