Diethylamine → N,N-diethyl-5-(1-methyl-1,2,3,4-tetrazol-5-yl)valeramide

HRID 35261Notes

Reaction equation

HRID 35261 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[N:5][N:4]=[N:3]1.[CH2:14]([N:16](CC)[CH2:17][CH3:18])[CH3:15].ClC(OCC(C)C)=O.C(NCC)C>CN(C)C=O>[CH2:14]([N:16]([CH2:17][CH3:18])[C:11](=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1[N:2]([CH3:1])[N:3]=[N:4][N:5]=1)[CH3:15]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 132034015-(1-Methyl-1,2,3,4-tetrazol-5-yl)valeric acid

Product 1

HCID 13142190N,N-diethyl-5-(1-methyl-1,2,3,4-tetrazol-5-yl)valeramideYield 29.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(5-(1-Methyl-1,2,3,4-tetrazol-5-yl)valeric acid (1.8 g) is dissolved in dimethylformamide (50 ml), and thereto is added triethylamine (1.1 g). To the mixture is added dropwise with stirring isobutyl chloroformate (1.5 g) under ice-cooling, and the mixture is stirred at room temperature for 30 minutes. To the mixture is added dropwise with stirring diethylamine (0.9 g) at rood temperature, and the mixture is stirred for 2 hours. Dimethylformamide is distilled off under reduced pressure, and the residue is purified by column chromatography (Wakogel C-200). After eluting with benzene-chloroform (1:1), the eluate is distilled under reduced pressure to give N,N-diethyl-5-(1-methyl-1,2,3,4-tetrazol-5-yl)valeramide (0.7 g), colorless liquid, b.p. 190°-200° C. (bath temperature)/0.07 mmHg, nD25 =1.4907.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred for 2 hours
  3. distillationDimethylformamide is distilled off under reduced pressure
  4. customthe residue is purified by column chromatography (Wakogel C-200)
  5. washAfter eluting with benzene-chloroform (1:1)
  6. distillationthe eluate is distilled under reduced pressure

Sources & evidence

ORD record
ord-918dd0690f82437b87a16fe418e53ad5
Source dataset
uspto-grants-1988_08
Patent number
US04766120

Reaction notes

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