Diethylamine → 1H-Tetrazole-1-butanamide, N,N-diethyl-5-methyl-

HRID 1758295Notes

Reaction equation

HRID 1758295 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[N:5]=[N:4][N:3]=1.[CH2:13]([N:15](CC)[CH2:16][CH3:17])[CH3:14].ClC(OCC(C)C)=O.C(NCC)C>CN(C)C=O>[CH2:13]([N:15]([CH2:16][CH3:17])[C:10](=[O:12])[CH2:9][CH2:8][CH2:7][N:6]1[C:2]([CH3:1])=[N:3][N:4]=[N:5]1)[CH3:14]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 12806313HCID 12806313, compound

Product 1

HCID 30619711H-Tetrazole-1-butanamide, N,N-diethyl-5-methyl-Yield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(5-Methyl-1,2,3,4-tetrazol-1-yl)butyric acid (1.7 g) is dissolved in dimethylformamide (50 ml) and triethylamine (1.1 g) is added to the solution. Isobutyl chloroformate (1.5 g) is added dropwise to the mixture with stirring and ice-cooling and the mixture is stirred at room temperature for 30 minutes. Diethylamine (0.9 g) is added dropwise to the mixture with stirring at room temperature. The mixture is stirred for 3 hours. Dimethylformamide is distilled off and the residue is purified by silica gel column chromatography (silica gel made of Merck & Co.). The column is eluted with chloroform-methanol (50:1) to obtain N,N-diethyl-4-(5-methyl-1,2,3,4-tetrazol-1-yl)butyric acid amide (1.4 g), b.p. 190°-200° C. (bath temperature)/0.04 mmHg, nD25 =1.4908.

Workup

  1. temperatureice-cooling
  2. stirringthe mixture is stirred at room temperature for 30 minutes
  3. stirringwith stirring at room temperature
  4. stirringThe mixture is stirred for 3 hours
  5. distillationDimethylformamide is distilled off
  6. customthe residue is purified by silica gel column chromatography (silica gel made of Merck & Co.)
  7. washThe column is eluted with chloroform-methanol (50:1)

Sources & evidence

ORD record
ord-9bc0585c92f64776af8b4bd7490b5172
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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