1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate → 5,6-Dichloro-4-fluoro-N-(1-methylethyl)-1H-benzimidazol-2-amine

HRID 2227189Notes

Reaction equation

HRID 2227189 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[C:3]=1[F:11].[CH:12]([N:15]=[C:16]=S)([CH3:14])[CH3:13].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:7]([Cl:8])=[CH:6][C:5]2[NH:9][C:16]([NH:15][CH:12]([CH3:14])[CH3:13])=[N:10][C:4]=2[C:3]=1[F:11]

Participants

5

Reactant 3

HCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 75263Isopropyl IsothiocyanateHCID 184721084,5-Dichloro-3-fluoro-1,2-phenylenediamine

Product 1

HCID 184721125,6-Dichloro-4-fluoro-N-(1-methylethyl)-1H-benzimidazol-2-amineYield 31%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4,5-Dichloro-3-fluoro-1,2-phenylenediamine (3.37 g, 17.28 mmol), isopropyl isothiocyanate (2.10 g, 20.76 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (9.52 g, 22.48 mmol) and pyridine (100 mL) were used according to general procedure I. The title compound was recrystallized from 1,4-dioxane to provide a tan solid (1.40 g, 31%); m.p. 212-215° C.; 1H NMR (DMSO-d6) δ: 11.15 (br s, 1H, NH), 7.21 (s, 1H, Ar—H), 6.99 (d, J=7.8 Hz, 1H, NH), 3.92 (m, 1H, CH), 1.21 (d, J=6.4 Hz, 6H, overlapping CH3).

Workup

  1. customThe title compound was recrystallized from 1,4-dioxane

Sources & evidence

ORD record
ord-8eb45fd012f64548ad90f074cc8b0cb0
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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