Hexamethylenetetramine → 2-Hydroxy-5-tetrazol-1-yl-benzaldehyde
Reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:25](O)=[O:26]>>[OH:12][C:9]1[CH:8]=[CH:7][C:6]([N:1]2[CH:5]=[N:4][N:3]=[N:2]2)=[CH:11][C:10]=1[CH:25]=[O:26]Participants
4
Procedure
A solution of 4-tetrazol-1-yl-phenol (0.01 mol) in trifluoroacetic acid (20 ml) and hexamethylenetetramine (0.04 mol) was heated at 70° for 18 h, cooled to room temperature and quenched with 2N solution of sulfuric acid (50 ml). The mixture was extracted with ethyl acetate (3×100 ml), dried (MgSO4), filtered and concentrated to give a residue which was purified by FCC (dichloromethane/methanol (9:1)) to afford the title compound in 30% yield.
Workup
- customquenched with 2N solution of sulfuric acid (50 ml)
- extractionThe mixture was extracted with ethyl acetate (3×100 ml)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customto give a residue which
- customwas purified by FCC (dichloromethane/methanol (9:1))
Sources & evidence
- ORD record
- ord-cacf794c7fdc422599f59791ce12e3f7
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05843966
Reaction notes
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