Water → HCID 11353613, compound

HRID 1768044Notes

Reaction equation

HRID 1768044 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][C:6]1[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH:8]=[CH:9][N:10]=1.Cl[CH2:23][C:24]1[N:25]=[C:26]([CH:29]=[CH:30][C:31]2[CH:36]=[CH:35][C:34]([S:37]([F:42])([F:41])([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)[O:27][CH:28]=1.O>CN(C=O)C>[F:40][S:37]([F:38])([F:39])([F:41])([F:42])[C:34]1[CH:35]=[CH:36][C:31](/[CH:30]=[CH:29]/[C:26]2[O:27][CH:28]=[C:24]([CH2:23][O:21][C:18]3[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][CH2:12][CH2:11][N:7]4[CH:8]=[CH:9][N:10]=[C:6]4[CH2:5][CH2:4][OH:3])=[CH:20][CH:19]=3)[N:25]=2)=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 222593234-[4-[2-(2-hydroxyethyl)-1H-imidazol-1-yl]butyl]phenolHCID 865985174-Chloromethyl-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazole

Product 1

HCID 11353613HCID 11353613, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14 mg (0.50 mmol) 95% sodium hydride were given to a solution of 130 mg (0.50 mmol) 4-{4-[2-(2-Hydroxyethyl)-imidazol-1-yl]-butyl}-phenol in 4.0 ml DMF and stirred for 15 min. 168 mg (0.50 mmol) 4-chloromethyl-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazole were added and stirring continued at r.t. overnight. After addition of 10 ml water the resulting precipitate was filtered, dried and purified by chromatography on silica (ethyl acetate/methanol 8:1) to give 133 mg (47%) amorphous material.

Workup

  1. stirringstirring
  2. waitcontinued at r.t. overnight
  3. filtrationwas filtered
  4. customdried
  5. custompurified by chromatography on silica (ethyl acetate/methanol 8:1)

Sources & evidence

ORD record
ord-2c843d25fa6b47f9a837180301901cb7
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

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