1-(3-Amino-2-methylaminophenyl) 3-mesitylthiourea → N2-Mesityl-1-methyl-1H-benzimidazole-2,7-diamine

HRID 2235533Notes

Reaction equation

HRID 2235533 reaction equation
[NH2:1][C:2]1[C:3]([NH:21][CH3:22])=[C:4]([NH:8][C:9]([NH:11][C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])=S)[CH:5]=[CH:6][CH:7]=1>C(#N)C.C(OCC)(=O)C.[Hg](Cl)Cl>[C:13]1([CH3:20])[CH:14]=[C:15]([CH3:19])[CH:16]=[C:17]([CH3:18])[C:12]=1[NH:11][C:9]1[N:21]([CH3:22])[C:3]2[C:2]([NH2:1])=[CH:7][CH:6]=[CH:5][C:4]=2[N:8]=1

Participants

5

Reactant 1

HCID 866129961-(3-Amino-2-methylaminophenyl) 3-mesitylthiourea

Product 1

HCID 86049130N2-Mesityl-1-methyl-1H-benzimidazole-2,7-diamineYield 55%

Reagents, catalysts & solvents 3

HCID 24085Mercuric ChlorideCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution containing 0.25 g (0.79 mmol) of 1-(3-amino-2-methylaminophenyl)-3-mesitylthiourea in acetonitrile was added 0.52 g (1.6 mmol) of mercury (II) chloride, and the mixture stirred for 1 h. The reaction mixture was diluted with ethyl acetate (2 ml) and filtered through a prepacked celite column. The filtrate was concentrated under reduced pressure and the residue purified via Biotage chromatography eluting with 20% ethyl acetate/dichloromethane to afford 0.12 g (55%) of product.

Workup

  1. filtrationfiltered through a prepacked celite column
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue purified via Biotage chromatography
  4. washeluting with 20% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-3f427345b33f472eb827719d7fb363f4
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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