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

HRID 978021

Reaction equation

HRID 978021 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][CH2:9][C:10](O)=[S:11])=[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>O1CCCC1>[CH2:13]([N:15]([CH2:16][CH3:17])[C:10](=[S:11])[CH2:9][CH2:8][CH2:7][C:6]1[N:2]([CH3:1])[N:3]=[N:4][N:5]=1)[CH3:14]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 178482013HCID 178482013, compound

Product 1

HCID 21153948N,N-diethyl-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramideYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(1-Methyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid (2 g) is dissolved in dry tetrahydrofuran (30 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. The mixture is stirred at room temperature for 30 minutes. To the mixture is further added dropwise with stirring diethylamine (0.9 g) at room temperature, and the mixture is stirred for 2 hours. The mixture is concentrated under reduced pressure, and the resulting residue is purified by subjecting it to column chromatography (Kieselgel 60, made by Merck & Co.). By eluting with n-hexane-ethyl acetate (1:1), there is obtained N,N-diethyl-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (1.4 g), colorless liquid, nD17.5 =1.5227

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred for 2 hours
  3. concentrationThe mixture is concentrated under reduced pressure
  4. customthe resulting residue is purified
  5. washBy eluting with n-hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-69463ce0d61e4188b54cdf080fab327d
Source dataset
uspto-grants-1987_05
Patent number
US04663323

Linked notes

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