1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate → 2-(Cyclopropylamino)-5,6-dichloro-1H-benzimidazole

HRID 2227169Notes

Reaction equation

HRID 2227169 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.[CH:11]1([N:14]=[C:15]=S)[CH2:13][CH2:12]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C[N+]1(CCN=C=NC2CCCCC2)CCOCC1>N1C=CC=CC=1>[CH:11]1([NH:14][C:15]2[NH:9][C:5]3[CH:6]=[C:7]([Cl:8])[C:2]([Cl:1])=[CH:3][C:4]=3[N:10]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 792974,5-Dichloro-1,2-phenylenediamineHCID 92463Cyclopropyl isothiocyanate

Product 1

HCID 105142812-(Cyclopropylamino)-5,6-dichloro-1H-benzimidazoleYield 70.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4,5-Dichloro-1,2-phenylenediamine (6.04 g, 34.1 mmol), cyclopropyl isothiocyanate (3.69 g, 37.2 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (20.1 g, 47.4 mmol) and pyridine (135 mL) were used according to general procedure I. The product was recrystallized from acetonitrile to afford 5.82 g (70%) of a yellow solid; m.p. 223-225° C. 1H NMR (DMSO-d6) δ: 11.2 (s, 1H, NH), 7.43 (s, 1H, NH), 7.27 (s, 2H, ArH), 2.49 (m, 1H, CH), 0.70 (m, 2H, CH), 0.49 (m, 2H, CH).

Workup

  1. customThe product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-fbea34706b534fdb89809ace1752cd5f
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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