Imidazole → HCID 59680507, compound

HRID 1393855Notes

Reaction equation

HRID 1393855 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][C:15](O)=[O:16])=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.N1C=CN=C1.[H-].[Na+].[NH2:39][C:40]1[S:41][S:42][C:43](=[S:45])[N:44]=1>O1CCCC1.O>[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][C:15]([NH:39][C:40]2[S:41][S:42][C:43](=[S:45])[N:44]=2)=[O:16])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 795Imidazole2×HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 2735329Xanthane hydrideHCID 11974810Benzeneacetic acid, 2-[(4-fluorophenyl)methoxy]-

Product 1

HCID 59680507HCID 59680507, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

2-{2-[(4-Fluorobenzyl)oxy]phenyl}acetic acid (1.04 g, 3.99 mmol) was dissolved in tetrahydrofuran (13 ml), and 1,1′-carbonyidiimidazole (0.777 g, 4.79 mmol) was added thereto. The imidazole mixture was stirred for 1 hour at room temperature. Sodium hydride (60% oil suspension 0.160 g, 3.99 mmol) was suspended in tetrahydrofuran (13 ml), and 3-amino-1,2,4-dithiazole-5-thione (0.601 g, 3.99 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 16 hours at room temperature. The reaction mixture, with water added thereto, was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over MgSO4, and then concentrated. The obtained residue was purified by silica gel chromatography (chloroform), to give 2-{2-[(4-fluorobenzyl)oxy]phenyl}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide (Compound 7) (0.523 g, 33%).

Workup

  1. stirringwas stirred for 16 hours at room temperature
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe obtained residue was purified by silica gel chromatography (chloroform)

Sources & evidence

ORD record
ord-7111a6ea6f0e459a83e5acec5735d8ea
Source dataset
uspto-grants-2008_03
Patent number
US07348017B2

Reaction notes

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