Imidazole → HCID 59309734, compound

HRID 1513004Notes

Reaction equation

HRID 1513004 reaction equation
[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]

Participants

10

Reactant 6

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

Product 2

HCID 59309734HCID 59309734, compoundHCID 68513900HCID 68513900, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-f51f96e845aa477997d9b2841b477228
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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