p-Toluenesulfonic acid → 2-(Isopropylamino)-4,5,6-trichloro-1H-benzimidazole

HRID 1167079Notes

Reaction equation

HRID 1167079 reaction equation
[Cl:1][C:2]1[C:3]([NH2:11])=[C:4]([NH2:10])[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].[CH:12]([N:15]=[C:16]=S)([CH3:14])[CH3:13].N=C=N.CC1C=CC(S(O)(=O)=O)=CC=1>N1C=CC=CC=1>[CH:12]([NH:15][C:16]1[NH:10][C:4]2[CH:5]=[C:6]([Cl:9])[C:7]([Cl:8])=[C:2]([Cl:1])[C:3]=2[N:11]=1)([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 75263Isopropyl IsothiocyanateHCID 1005293,4,5-Trichlorobenzene-1,2-diamineHCID 160435Carbodiimide

Product 1

HCID 105405952-(Isopropylamino)-4,5,6-trichloro-1H-benzimidazoleYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,4,5-Trichloro-1,2-phenylenediamine (3.12 g, 14.8 mmol), isopropyl isothiocyanate (1.62 g, 16.0 mmol), 1-cyclohexyl-3-2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (8.4 g, 19.9 mmol), and pyridine (50 mL) were used according to general procedure II. The product was recrystallized from 1,4-dioxane to give 2.9 g (72%) of a tan solid. MS (CI): m/z 276 (M+1). Anal. Calcd. for C10H10Cl3N3-(0.10 C4H8O2): C, 43.47; H, 3.79; N, 14.62. Found. C, 43.70; H, 3.89; N, 14.43.

Workup

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

Sources & evidence

ORD record
ord-6ec55008ed134881b36720576db65c73
Source dataset
uspto-grants-2003_09
Patent number
US06617315B1

Reaction notes

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