Imidazole → HCID 59680503, compound

HRID 1393860Notes

Reaction equation

HRID 1393860 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[CH:20][CH:19]=3)[C:15](O)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.N1C=CN=C1.[H-].[Na+].[NH2:54][C:55]1[S:56][S:57][C:58](=[S:60])[N:59]=1.O.[Cl-].[NH4+]>O1CCCC1>[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[CH:20][CH:19]=3)[C:15]([NH:54][C:55]3[S:56][S:57][C:58](=[S:60])[N:59]=3)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 6

HCID 795Imidazole2×HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 2735329Xanthane hydrideHCID 57429219Ammonium chloride monohydrateHCID 69310221HCID 69310221, compound

Product 1

HCID 59680503HCID 59680503, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

2,2-Bis{4-[(4-fluorobenzyl)oxy]phenyl}acetic acid (1.00 g, 2.17 mmol) was dissolved in tetrahydrofuran (7 ml), and 1,1′-carbonyldiimidazole (0.423 g, 2.61 mmol) was added thereto. The imidazole mixture was stirred for 1 hour at room temperature. Sodium hydride (60% oil suspension 0.087 g, 2.17 mmol) was suspended in tetrahydrofuran (7 ml), and 3-amino-1,2,4-dithiazole-5-thione (0.326 g, 2.17 mmol) was added thereto. After being stirred for 30 minutes at 0° C., the reaction mixture, with the imidazole mixture added thereto, was stirred for 17 hours at room temperature. The reaction mixture, with saturated ammonium chloride water added thereto, was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate water and saturated brine successively, dried over MgSO4, and then concentrated. The obtained residue was purified by silica gel column chromatography (chloroform), to give 2,2-bis{4-[(4-fluorobenzyl)oxy]phenyl}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide (Compound 11) (0.256 g, 20%).

Workup

  1. stirringwas stirred for 17 hours at room temperature
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate water and saturated brine successively
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-c63439127a974ef782178709cf197f82
Source dataset
uspto-grants-2008_03
Patent number
US07348017B2

Reaction notes

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