Imidazole → HCID 59309734, 화합물

HRID 1513004노트

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HRID 1513004 반응식
[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]

참가 물질

10

반응물 6

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 591999HCID 591999, 화합물HCID 6406993-amino-4-chlorobenzenethiolHCID 59309703HCID 59309703, 화합물HCID 68513900HCID 68513900, 화합물

생성물 2

HCID 59309734HCID 59309734, 화합물HCID 68513900HCID 68513900, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f51f96e845aa477997d9b2841b477228
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217069B2

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