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

HRID 1393856Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

2-{3-[(4-Fluorobenzyl)oxy]phenyl}acetic acid (1.00 g, 3.84 mmol) was dissolved in tetrahydrofuran (13 ml), and 1,1′-carbonyldiimidazole (0.748 g, 4.61 mmol) was added thereto. The imidazole mixture was stirred for 1 hour at 0° C. Sodium hydride (60% oil suspension 0.154 g, 3.84 mmol) was suspended in tetrahydrofuran (13 ml), and 3-amino-1,2,4-dithiazole-5-thione (0.577 g, 3.84 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 13 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-{3-[(4-fluorobenzyl)oxy]phenyl}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide (Compound 8) (0.097 g, 6%).

Workup

stirringwas stirred for 13 hours at room temperature
extractionwas extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe obtained residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record: ord-e60ca1a391ee4704af58e4af0c53c144
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348017B2

Reaction notes

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