4-(Trifluoromethyl)phenyl isocyanate → 1-(4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)-1-n-hexyl-3-{4-(trifluoromethyl)phenyl]urea

HRID 412335ノート

反応式

HRID 412335 の反応式
[CH2:1]([NH:7][C:8]1[CH:40]=[CH:39][C:11]([O:12][C:13]2[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]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[F:41][C:42]([F:53])([F:52])[C:43]1[CH:48]=[CH:47][C:46]([N:49]=[C:50]=[O:51])=[CH:45][CH:44]=1>O1CCCC1>[O:33]=[C:31]1[NH:30][C:29](=[O:34])[CH:28]([CH2:27][C:26]2[CH:35]=[CH:36][C:23]([O:22][CH2:21][C:19]3[N:18]([CH3:37])[C:17]4[CH:38]=[C:13]([O:12][C:11]5[CH:39]=[CH:40][C:8]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:50]([NH:49][C:46]6[CH:45]=[CH:44][C:43]([C:42]([F:41])([F:52])[F:53])=[CH:48][CH:47]=6)=[O:51])=[CH:9][CH:10]=5)[CH:14]=[CH:15][C:16]=4[N:20]=3)=[CH:24][CH:25]=2)[S:32]1

参加物

4

反応物 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 865877705-[4-[6-(4-n-Hexylaminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4dione

生成物 1

HCID 185376011-(4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)-1-n-hexyl-3-{4-(trifluoromethyl)phenyl]urea

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 5-[4-[6-(4-n-hexylaminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione (0.39 g), α,α,α-trifluoro-p-tolyl isocyanate (0.15 g) and anhydrous tetrahydrofuran (20 ml) was allowed to stand at room temperature for 2 days. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The extract was dried over anhydrous sodium sulfate and then concentrated. The residue was reprecipitated from a mixture of ether and diisopropyl ether to afford the title compound (0.37 g, Rf=0.49: thin layer chromatography on a silica gel plate using ethyl acetate:n-hexane=2:1 as the eluant).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was reprecipitated from a mixture of ether and diisopropyl ether

出典と根拠

ORDレコード
ord-40bac1ee6e354d54b410ccdaeae3741d
出典データセット
uspto-grants-2003_05
特許番号
US06562849B1

反応ノート

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