p-Toluenesulfonic acid → 4,6-Dichloro-N-(propan-2-yl)-1H-benzimidazol-2-amine

HRID 1167089Notes

Reaction equation

HRID 1167089 reaction equation
[Cl:1][C:2]1[C:3]([NH2:10])=[C:4]([NH2:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:11]([N:14]=[C:15]=S)([CH3:13])[CH3:12].CC1C=CC(S(O)(=O)=O)=CC=1>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]2[N:10]=[C:15]([NH:14][CH:11]([CH3:13])[CH3:12])[NH:9][C:4]=2[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 75263Isopropyl IsothiocyanateHCID 42768353,5-Dichlorobenzene-1,2-diamine

Product 1

HCID 229954404,6-Dichloro-N-(propan-2-yl)-1H-benzimidazol-2-amineYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,5-Dichloro-1,2-phenylenediamine (1.30 g, 7.32 mmol), isopropyl isothiocyanate (0.81 g, 8.00 mmol), 1-cyclohexyl-1-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (4.19 g, 9.89 mmol) and pyridine (25 mL) were used according to general procedure I. The product was recrystallized from 1,4-dioxane to afford 1.07 g (60%) of a white solid. Anal. calcd for C10H11Cl12N3-(0.25 C4H8O2): C, 49.64; H, 4.92; N, 15.79. Found: C, 49.54; H, 4.94; N, 15.79.

Workup

  1. customThe product was recrystallized from 1,4-dioxane

Sources & evidence

ORD record
ord-c604254bdf394f2c87cdb80dddb6d7a1
Source dataset
uspto-grants-2003_09
Patent number
US06617315B1

Reaction notes

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