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

HRID 2227177Notes

Reaction equation

HRID 2227177 reaction equation
[Cl:1][C:2]1[C:3]([NH2:10])=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:11]([N:14]=[C:15]=S)([CH3:13])[CH3:12].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:10]=[C:15]([NH:14][CH:11]([CH3:13])[CH3:12])[NH:9][C:4]=2[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 75263Isopropyl IsothiocyanateHCID 108450203,4-Dichlorobenzene-1,2-diamine

Product 1

HCID 184219284,5-Dichloro-N-(1-methylethyl)-1H-benzimidazol-2-amineYield 55.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,4-Dichloro-1,2-phenylenediamine (8.00 g, 45.19 mmol), isopropyl isothiocyanate (5.26 g, 51.99 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (25.0, 59.02 mmol), and pyridine (250 mL) were used according to general procedure I. The product was recrystallized from 1,4-dioxane to afford 6.12 g (55%) of a white solid. MS (EI): m/z 244 (M+H); 1H NMR (DMSO-d6) δ: 11.08 (s, 1H, NH), 7.07 (d, J=8.3Hz, 1H, ArH), 7.00 (brs, 1H, NH), 6.99 (d, J=8.3Hz, 1H, ArH), 3.91 (m, 1H, CH), 1.21 (d, J=6.5 Hz, 6H, overlapping CH3).

Workup

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

Sources & evidence

ORD record
ord-5da95678b2f34dce8c879b7ff6bea135
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

Loading…