Dimethylformamide → 5-(4-(4-Methoxy-phenyl)-butyl)-2H-tetrazole

HRID 1768051Notes

Reaction equation

HRID 1768051 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].[N-:15]=[N+:16]=[N-:17].[Na+].[Cl-].[NH4+].C[N:22](C=O)C>C(OCC)(=O)C.O>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:1][CH2:2][CH2:3][CH2:4][C:5]2[N:15]=[N:16][NH:17][N:22]=2)=[CH:8][CH:9]=1.[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:1][CH2:2][CH2:3][CH2:4][C:5]2[N:15]=[N:16][NH:17][CH:6]=2)=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 236145351-Hex-5-ynyl-4-methoxy-benzene

Product 2

HCID 236145535-(4-(4-Methoxy-phenyl)-butyl)-2H-tetrazoleHCID 178490075HCID 178490075, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.80 g (9.56 mmol) 1-hex-5-ynyl-4-methoxy-benzene, 1.86 g (28.6 mmol) sodium azide, 1.53 g (28.6 mmol) ammonium chloride and 80 ml DMF was kept at 125° C. for 7 d with an extra addition of 1.80 g sodium azide and 1.53 g ammonium chloride every day. After cooling to r.t. the dark reaction mixture was distributed between water and ethyl acetate. The organic phase was dried over sodium sulphate and the solvent distilled off. The residue was separated by HPLC on a RP18-endcapped column (methanol/water) (a reversed phase column which is used with methanol/water as eluent) to yield 450 mg 5-(4-(4-Methoxy-phenyl)-butyl)-2H-tetrazole and 500 mg 4-(4-(4-Methoxy-phenyl)-butyl)-1H-[1,2,3]triazole

Workup

  1. customthe dark reaction mixture
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. distillationthe solvent distilled off
  4. customThe residue was separated by HPLC on a RP18-endcapped column (methanol/water) (a reversed phase column which

Sources & evidence

ORD record
ord-a2eaf087ce5d4f64ad5fffa48b6628ef
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

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