Imidazole → HCID 86610505, compound

HRID 2109986Notes

Reaction equation

HRID 2109986 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][NH2:13])[CH2:8][CH2:7]1.[C:18]([N:25]1[CH:29]=[CH:28][N:27]=C1)(N1C=CN=C1)=[S:19].N1C=CN=C1.[N+]([C:38]1[C:39](N)=C(N)C=[CH:42][CH:43]=1)([O-])=O>C(#N)C>[NH2:27][C:28]1[CH:42]=[CH:43][CH:38]=[CH:39][C:29]=1[NH:25][C:18]([NH:13][CH2:12][CH:9]1[CH2:10][CH2:11][N:6]([CH2:5][C:4]2[CH:14]=[CH:15][C:16]([Cl:17])=[C:2]([Cl:1])[CH:3]=2)[CH2:7][CH2:8]1)=[S:19]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 802641,1'-ThiocarbonyldiimidazoleHCID 43595253-Nitro-1,2-phenylenediamineHCID 43130924HCID 43130924, compound

Product 1

HCID 86610505HCID 86610505, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After dissolving C-[1-(3,4-dichloro-benzyl)-piperidin-4-yl]-methylamine (80 mg) in acetonitrile (2 ml), thiocarbonyldiimidazole (80 mg) and imidazole (6 mg) were added at 0° C. The mixture was stirred at room temperature for 2 hours and 30 minutes, and then 3-nitro-1,2-phenylenediamine (66 mg) was added and the temperature was raised to 50° C. prior to stirring for 12 hours. The reaction mixture was filtered, the solvent was removed under reduced pressure, and the obtained residue was purified by thin-layer silica gel chromatography (hexane/ethyl acetate/dichloromethane/methanol=60/25/10/5) to obtain 1-(2-amino-phenyl-3-[1-(3,4-dichloro-benzyl)-piperidin-4-ylmethyl]-thiourea. The compound was identified by LC-MS.

Workup

  1. additionwere added at 0° C
  2. temperaturethe temperature was raised to 50° C.
  3. stirringto stirring for 12 hours
  4. filtrationThe reaction mixture was filtered
  5. customthe solvent was removed under reduced pressure
  6. customthe obtained residue was purified by thin-layer silica gel chromatography (hexane/ethyl acetate/dichloromethane/methanol=60/25/10/5)

Sources & evidence

ORD record
ord-4667f8f92559421094605fe05c1eb564
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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