Benzyl Alcohol → Benzyl tetrazole-1-acetate

HRID 1733678Notes

Reaction equation

HRID 1733678 reaction equation
[N:1]1([CH2:6][C:7]([OH:9])=[O:8])[CH:5]=[N:4][N:3]=[N:2]1.[CH2:10](O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1C=CC=CC=1.ClC1C=CC(S(ON2C3C=C(Cl)C=CC=3N=N2)(=O)=O)=CC=1>C(C)#N.C(OCC)(=O)C.O>[N:1]1([CH2:6][C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH:5]=[N:4][N:3]=[N:2]1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 5432071-Tetrazolylacetic acidHCID 122228411-(p-Chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole

Product 1

HCID 12222850Benzyl tetrazole-1-acetateYield 74.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrazole-1-acetic acid (0.64 g), benzyl alcohol (0.65 g) and pyridine (0.80 ml) are dissolved in dry cyanomethane (10 ml) and thereto is added 1-(p-chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole (1.72 g) under ice-cooling. After allowing to stand overnight, to the mixture are added water and ethyl acetate. The ethyl acetate layer is washed, dried and concentrated. The precipitated crystals are washed well with ether-petroleum ether to give benzyl tetrazole-1-acetate (815 mg), melting point: 69°-72° C.

Workup

  1. temperaturecooling
  2. washThe ethyl acetate layer is washed
  3. customdried
  4. concentrationconcentrated
  5. washThe precipitated crystals are washed well with ether-petroleum ether

Sources & evidence

ORD record
ord-e3a6b0afc9324caa9aeace178db71eb7
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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