Benzenemethanamine, 3,4-dichloro- → HCID 68540030, compound

HRID 1993911Notes

Reaction equation

HRID 1993911 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH2:6].[IH:11].CS[C:14]1[NH:15][CH2:16][CH2:17][N:18]=1>CO>[IH:11].[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH:6][C:14]1[NH:18][CH2:17][CH2:16][N:15]=1

Participants

4

Reactant 2

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 122212281H-Imidazole, 4,5-dihydro-2-(methylthio)-, hydriodide (1:1)

Product 1

HCID 68540030HCID 68540030, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,4-dichlorobenzylamine (0.352 g, 2.0 mmol) in methanol (5 ml) was added 2-methylthio-2-imidazoline hydroiodide (0.488 g, 2.0 mmol) and the mixture was heated to reflux for 4 h. The solvent was partly removed by evaporation (to approx. 1 ml) and ether (5 ml) was added. After stirring for 15 min the precipitating white solid was removed by filtration and washed with ether. It was obtained 130 mg (18%) of a white solid; MS (ISP): 244.1; 246.0 ([M+H]+.).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 h
  3. customThe solvent was partly removed by evaporation (to approx. 1 ml) and ether (5 ml)
  4. additionwas added
  5. customwas removed by filtration
  6. washwashed with ether

Sources & evidence

ORD record
ord-b19212c416544f0cbfd24bb8b1844220
Source dataset
uspto-grants-2010_01
Patent number
US07652055B2

Reaction notes

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