Methyl formate → N-[[5-[(Dipropylamino)methyl]-1,2,4-oxadiazol-3-yl]methyl]formamide

HRID 1378117Notes

Reaction equation

HRID 1378117 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([CH2:8][N:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])[O:5][N:4]=1.[CH:16](OC)=[O:17]>>[CH2:10]([N:9]([CH2:8][C:6]1[O:5][N:4]=[C:3]([CH2:2][NH:1][CH:16]=[O:17])[N:7]=1)[CH2:13][CH2:14][CH3:15])[CH2:11][CH3:12]

Participants

3

Reactant 2

HCID 7865Methyl formateHCID 22914390HCID 22914390, compound

Product 1

HCID 22914380N-[[5-[(Dipropylamino)methyl]-1,2,4-oxadiazol-3-yl]methyl]formamideYield 79%

Procedure

A solution of 15.6 g (73.5 mmol) of (3-aminomethyl-1,2,4-oxadiazol-5-ylmethyl)-dipropylamine in 100 ml of methyl formate was heated at reflux for seven hours. Subsequently, the solution was evaporated and the residue was chromatographed (silica gel, methylene chloride/methanol 19:1). There were obtained 14 g (79%) of N-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-ylmethyl)-formamide, Rf=0.28 (silica gel, methylene chloride/methanol 19:1).

Workup

  1. temperatureat reflux for seven hours
  2. customSubsequently, the solution was evaporated
  3. customthe residue was chromatographed (silica gel, methylene chloride/methanol 19:1)

Sources & evidence

ORD record
ord-fdd359d1c4c64c1fbac2655a72940714
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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