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

HRID 750953Notes

Reaction equation

HRID 750953 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 PUROSPHER® STAR RP-18 endcapped from Merk KGaA, Darmstadt, Germany, 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 PUROSPHER® STAR RP-18

Sources & evidence

ORD record
ord-fe2f587ef61d4b6e918ac6fedc3f74c2
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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