Diethyl Ether → HCID 178480598, compound

HRID 2052068Notes

Reaction equation

HRID 2052068 reaction equation
I.[CH3:2][N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[NH:8][C:9](SC)=[N:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.CCOCC>CC(O)(C)C>[CH3:2][N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[NH:8][C:9]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[N:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8083MorpholineHCID 178503857HCID 178503857, compound

Product 1

HCID 178480598HCID 178480598, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 1.5 g (0.004 mole) of methyl N-(1-methylimidazol-2-yl)-N'-phenylcarbamimidothioate hydroiodide and 0.73 g (0.0084 mole) of morpholine in 30 ml of t-BuOH is refluxed overnight. Upon cooling, ether is added and morpholine hydroiodide is removed by filtration. The filtrate is taken to dryness and the residue is taken up in CH2Cl2 and converted to the free base with 3 N NaOH. The organic layer is separated, dried over K2CO3, filtered and the solvent is removed in vacuo to give a residue of N-(1-methylimidazol-2-yl)-N'-phenyl-4-morpholine carboximidamide, which is taken up in acetone and converted to the hydrochloride salt with ethereal HCl.

Workup

  1. temperatureUpon cooling
  2. custommorpholine hydroiodide is removed by filtration
  3. customThe organic layer is separated
  4. dry with materialdried over K2CO3
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-997af10904894ca4b15c804bffaaa73a
Source dataset
uspto-grants-1980_01
Patent number
US04182865

Reaction notes

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