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

HRID 2227175Notes

Reaction equation

HRID 2227175 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.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]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 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-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; 1H NMR (DMSO-d6) δ: 10.9 (s, 1H, NH), 7.07 (d, J=1.5 Hz, 1H, ArH), 6.98 (d, J=1.6 Hz, 1H, ArH), 6.92 (d, J=7.9 Hz, 1H, NH), 3.89 (m, 1H, CH), 1.17 (d, J=6.6 Hz, 6H, overlapping CH3).

Workup

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

Sources & evidence

ORD record
ord-d2c626b9bb514856a54af6bfdb69d706
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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