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

HRID 35249

Reaction equation

HRID 35249 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-hexaneethyl 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-hexaneethyl acetate (1:1)

Sources & evidence

ORD record
ord-78fb2885d3ea475e8b0b26aab8d14d29
Source dataset
uspto-grants-1988_08
Patent number
US04766120

Linked notes

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