Hydrochloric Acid → N-(3-(S-ethylisothioureido)phenylmethyl)dimethylamine

HRID 1861951Notes

Reaction equation

HRID 1861951 reaction equation
[NH:1]([C:5]1[CH:6]=[C:7]([CH2:11][N:12]([CH3:14])[CH3:13])[CH:8]=[CH:9][CH:10]=1)[C:2]([NH2:4])=[S:3].Cl.[CH2:16](I)[CH3:17]>C(#N)C.O1CCOCC1>[CH2:16]([S:3][C:2](=[NH:4])[NH:1][C:5]1[CH:6]=[C:7]([CH2:11][N:12]([CH3:14])[CH3:13])[CH:8]=[CH:9][CH:10]=1)[CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 18621787(3-Dimethylaminomethyl-phenyl)-thiourea

Product 1

HCID 178477474N-(3-(S-ethylisothioureido)phenylmethyl)dimethylamineYield 19%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the compound (43.5 mg) obtained in Example 40 in acetonitrile (5 ml), a solution of hydrogen chloride in 1,4-dioxane (4N, 0.1 ml) and ethyl iodide (50 mg) were added and heated under reflux for 5 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by basic silica gel column chromatography (eluent, methylene chloride methanol=5:1) to give 9.2 mg of the titled compound (yield, 19%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe resulting residue was purified by basic silica gel column chromatography (eluent, methylene chloride methanol=5:1)

Sources & evidence

ORD record
ord-079f0dcbbaa44a57b4d88d91e8f2aab7
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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