Sulfur → HCID 10215999, compound

HRID 2109987Notes

Reaction equation

HRID 2109987 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[CH2:15][CH2:14]1)=S.[S]>O=[Hg].C(O)C>[NH:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[NH:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 5362487SulfurHCID 86610505HCID 86610505, compound

Product 1

HCID 10215999HCID 10215999, compound

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 702EthanolSolvent

Procedure

After adding ethanol (1 ml) to 1-(2-amino-phenyl-3-[1-(3,4-dichloro-benzyl)-piperidin-4-ylmethyl]-thiourea (11 mg, 0.025 mmol), mercury (II) oxide red (16 mg, 0.074 mmol) and sulfur (0.3 mg, 0.0094 mmol) were added at room temperature, and the mixture was refluxed for 7 hours. The mercury was filtered with celite, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/dichloromethane/methanol/triethylamine=40/25/20/10/5) to obtain (1H-benzoimidazol-2-yl)-[1-(3,4-dichloro-benzyl)-piperidin-4-ylmethyl]-amine. The compound was identified by LC-MS.

Workup

  1. additionwere added at room temperature
  2. temperaturethe mixture was refluxed for 7 hours
  3. filtrationThe mercury was filtered with celite
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/dichloromethane/methanol/triethylamine=40/25/20/10/5)

Sources & evidence

ORD record
ord-94e21bee54a54e8d90088acca5c71bed
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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