Hexamethylenetetramine → 2-Hydroxy-5-tetrazol-1-yl-benzaldehyde

HRID 418364Notes

Reaction equation

HRID 418364 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

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 5429104-(1H-1,2,3,4-tetrazol-1-yl)phenol

Product 1

HCID 108453442-Hydroxy-5-tetrazol-1-yl-benzaldehydeYield 30%

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

  1. customquenched with 2N solution of sulfuric acid (50 ml)
  2. extractionThe mixture was extracted with ethyl acetate (3×100 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue which
  7. customwas purified by FCC (dichloromethane/methanol (9:1))

Sources & evidence

ORD record
ord-1cc13ec7537f4233b0069df253330fb5
Source dataset
uspto-grants-2012_01
Patent number
US08093268B2

Reaction notes

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