Imidazole → HCID 59680520, compound

HRID 1393865Notes

Reaction equation

HRID 1393865 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([O:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH3:24])[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+].[NH2:46][C:47]1[S:48][S:49][C:50](=[S:52])[N:51]=1.O.[Cl-].[NH4+]>O1CCCC1>[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([O:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH3:24])[C:15]([NH:46][C:47]3[S:48][S:49][C:50](=[S:52])[N:51]=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 69308438HCID 69308438, compound

Product 1

HCID 59680520HCID 59680520, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

2-{4-[(4-Fluorobenzyl)oxy]phenyl}-2-[(2-methoxyethoxy)methoxy]acetic acid (0.156 g, 0.429 mmol) was dissolved in tetrahydrofuran (1.4 ml), and 1,1′-carbonyidiimidazole (0.083 g, 0.514 mmol) was added thereto. The imidazole mixture was stirred1 hour at room temperature. Sodium hydride (60% oil suspension 0.021 g, 0.514 mmol) was suspended in tetrahydrofuran (1.4 ml), and 3-amino-1,2,4-dithiazole-5-thione (0.077 g, 0.514 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 saturated ammonium chloride 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 column chromatography (chloroform), to give 2-{4-[(4-fluorobenzyl)oxy]phenyl}-2-[(2-methoxyethoxy)methoxy]-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide (Compound 15) (0.139 g, 65%).

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 column chromatography (chloroform)

Sources & evidence

ORD record
ord-efd81fcc57d34a4d9ff2eb1ca7eb4536
Source dataset
uspto-grants-2008_03
Patent number
US07348017B2

Reaction notes

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