1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate → 4-Chloro-2-(isopropylamino)-1H-benzimidazole

HRID 1167086Notes

Reaction equation

HRID 1167086 reaction equation
[Cl:1][C:2]1[C:3]([NH2:9])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[CH:10]([N:13]=[C:14]=S)([CH3:12])[CH3:11].CC1C=CC(S([O-])(=O)=O)=CC=1.C[N+]1(CCN=C=NC2CCCCC2)CCOCC1>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]2[N:9]=[C:14]([NH:13][CH:10]([CH3:12])[CH3:11])[NH:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 75263Isopropyl IsothiocyanateHCID 3462489(2-Amino-3-chlorophenyl)amine

Product 1

HCID 229954304-Chloro-2-(isopropylamino)-1H-benzimidazoleYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Chloro-1,2-phenylenediamine (6.41 g, 44.95 mmol), isopropyl isothiocyanate (5.20 g, 51.6 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (25.0 g, 59.02 mmol) and pyridine (300 mL) were used according to general procedure I. The product was recrystallized from 1,4-dioxane afford 5.45 g (58%) of a brownish solid. MS (EI): m/z 210.1 (M+H). Anal. calcd for C10H12ClN3-(0.5 C4H8O2): C, 56.80; H, 6.36; N, 16.56. Found: C, 57.00; H, 6.34; N, 16.69.

Workup

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

Sources & evidence

ORD record
ord-373dd17f60f341a8ba9a33d20ba51b95
Source dataset
uspto-grants-2003_09
Patent number
US06617315B1

Reaction notes

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