Water → HCID 178450115, compound
Reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:33]=[CH:32][CH:31]=[CH:30][C:22]=4[O:23][CH:24]([CH2:27][CH2:28][CH3:29])[C:25]#[N:26])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[N-:34]=[N+:35]=[N-:36].[Na+].[Cl-].[NH4+].O>CN(C)C=O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:33]=[CH:32][CH:31]=[CH:30][C:22]=4[O:23][CH:24]([C:25]4[NH:36][N:35]=[N:34][N:26]=4)[CH2:27][CH2:28][CH3:29])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:2])([CH3:3])[CH3:4]Participants
Conditions
- Temperature
- 120 °C
Procedure
2-{2-{[2-(4-tert-Butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}pentanenitrile (430 mg) was dissolved in dimethylformamide (5 ml), and sodium azide (364 mg) and ammonium chloride (0.3 g) were added. The mixture was stirred at 120° C. for three hours. The reaction mixture was cooled and poured into water and extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate again and the combined organic layer was washed with brine and dried over magnesium sulfate. After concentration, the crude product was purified on a silica gel column (15 g) eluting with a mixed solvent of methylene chloride and methanol (2% vol.) to give 2-(4-tert-butylthiazol-2-yl)-5-{2-[1-(1H-tetrazol-5-yl)butoxy]phenylmethoxy}benzofuran (400 mg).
Workup
- temperatureThe reaction mixture was cooled
- extractionextracted with ethyl acetate
- extractionThe aqueous layer was extracted with ethyl acetate again
- washthe combined organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- concentrationAfter concentration
- customthe crude product was purified on a silica gel column (15 g)
- washeluting with a mixed solvent of methylene chloride and methanol (2% vol.)
Sources & evidence
- ORD record
- ord-771fd0a15eb342df9572643e26410ad2
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05994378
Reaction notes
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