Imidazole → 2-{4-[(4-fluorobenzyl)oxy]phenyl}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide

HRID 1393853Notes

Reaction equation

HRID 1393853 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][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+].[NH2:39][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][C:11]([CH2:14][C:15]([NH:39][C:40]3[S:41][S:42][C:43](=[S:45])[N:44]=3)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 795Imidazole2×HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 2735329Xanthane hydrideHCID 119750502-(4-((4-Fluorobenzyl)oxy)phenyl)acetic acid

Product 1

HCID 596805282-{4-[(4-fluorobenzyl)oxy]phenyl}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamideYield 33.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

2-{4-[(4-Fluorobenzyl)oxy]phenyl}acetic acid (1.00 g, 3.84 mmol) was dissolved in tetrahydrofuran (10 ml), and 1,1′-carbonyldiimidazole (0.748 g, 4.61 mmol) was added thereto. The imidazole mixture was stirred for 1 hour at room temperature. Sodium hydride (60% oil suspension 0.131 g, 3.27 mmol) was suspended in tetrahydrofuran (8 ml), and 3-amino-1,2,4-dithiazole-5-thione (0.491 g, 3.27 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 3 hours at room temperature. The 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 column chromatography (chloroform), to give 2-{4-[(4-fluorobenzyl)oxy]phenyl}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide (Compound 5) (0.431 g, 29%).

Workup

  1. stirringwas stirred for 3 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-2276e0aa01884ca6bf9fcd92f1216174
Source dataset
uspto-grants-2008_03
Patent number
US07348017B2

Reaction notes

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