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

HRID 1167085Notes

Reaction equation

HRID 1167085 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=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>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]2[NH:9][C:15]([NH:14][CH:11]([CH3:13])[CH3:12])=[N:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 75263Isopropyl IsothiocyanateHCID 27367551,2-Diamino-4,5-difluorobenzene

Product 1

HCID 229954245,6-Difluoro-2-(isopropylamino)-1H-benzimidazoleYield 53%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4,5-Difluoro-1,2-phenylenediamine (2.87 g, 19.91 mmol), isopropyl isothiocyanate (2.19 g, 21.65 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (11.38 g, 26.87 mmol) and pyridine (75 mL) were used according to general method I. The product was recrystallized from 1,4-dioxane to afford 2.23 g (53%) of a white solid; m.p. 188-189° C. Anal. Calcd for C10H11F2N3: C, 56.87; A, 5.25; N, 19.89. Found C, 56.95; H, 5.25; N, 19.98.

Workup

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

Sources & evidence

ORD record
ord-9ef1116391fb4206b40962569bd477d8
Source dataset
uspto-grants-2003_09
Patent number
US06617315B1

Reaction notes

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