Imidazole → HCID 59309734、化合物

HRID 1513004ノート

反応式

HRID 1513004 の反応式
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][C:3]=1[NH2:4].[C:10]([Si:14]([CH3:30])([CH3:29])[O:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25](O)([CH3:27])[CH3:26])([CH3:13])([CH3:12])[CH3:11].COC1C=CC=CC=1C(O)(C)C.[Cl:43][C:44]1[CH:50]=[CH:49][C:48]([S:51][C:52]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=2[O:61][CH2:62][CH2:63][OH:64])([CH3:54])[CH3:53])=[CH:47][C:45]=1[NH2:46].N1C=CN=C1.[Si](Cl)(C(C)(C)C)(C)C>CN(C)C=O.O>[Cl:43][C:44]1[CH:50]=[CH:49][C:48]([S:51][C:52]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=2[O:61][CH2:62][CH2:63][OH:64])([CH3:54])[CH3:53])=[CH:47][C:45]=1[NH2:46].[Si:14]([O:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([CH3:27])([S:9][C:6]1[CH:7]=[CH:8][C:2]([Cl:1])=[C:3]([CH:5]=1)[NH2:4])[CH3:26])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:29])[CH3:30]

参加物

10

反応物 6

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 591999HCID 591999、化合物HCID 6406993-amino-4-chlorobenzenethiolHCID 59309703HCID 59309703、化合物HCID 68513900HCID 68513900、化合物

生成物 2

HCID 59309734HCID 59309734、化合物HCID 68513900HCID 68513900、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

2-Chloro-5-{1-[2-(2-hydroxyethoxy)phenyl]-1-methylethylthio}aniline was prepared in a similar manner to that described in Reference Example 52 using 2-chloro-5-mercaptoaniline and 2-{2-[2-(tert-butyldimethyl silyloxy)ethoxy]phenyl}-2-propanol instead of 2-chloro-5-mercapto-4-methoxyaniline and 2-(2-methoxyphenyl)-2-propanol, respectively. To the solution of the obtained 2-chloro-5-{1-[2-(2-hydroxyethoxy)-phenyl]-1-methylethylthio}aniline (0.55 g) and imidazole (0.14 g) in N,N-dimethylformamide (3 mL) was added tert-butyldimethylsilyl chloride (0.24 g), and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=4/1) to give the title compound (0.66 g).

後処理

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-f51f96e845aa477997d9b2841b477228
出典データセット
uspto-grants-2012_07
特許番号
US08217069B2

反応ノート

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