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1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate → 2-(Cyclopropylamino)-4,5,6-trichloro-1H-benzimidazole

HRID 1532595
Notes
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Reaction equation

HRID 1532595 reaction equation
[Cl:1][C:2]1[C:3]([NH2:11])=[C:4]([NH2:10])[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].[CH:12]1([N:15]=[C:16]=S)[CH2:14][CH2:13]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C[N+]1(CCN=C=NC2CCCCC2)CCOCC1>N1C=CC=CC=1>[CH:12]1([NH:15][C:16]2[NH:10][C:4]3[CH:5]=[C:6]([Cl:9])[C:7]([Cl:8])=[C:2]([Cl:1])[C:3]=3[N:11]=2)[CH2:14][CH2:13]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 92463Cyclopropyl isothiocyanateHCID 1005293,4,5-Trichlorobenzene-1,2-diamine

Product 1

HCID 229954112-(Cyclopropylamino)-4,5,6-trichloro-1H-benzimidazoleYield 83.3%

Reagents, catalysts & solvents 1

HCID 1049Pyridine
Solvent

Procedure

3,4,5-Trichloro-1,2-phenylenediamine (3.02 g, 14.28 mmol), cyclopropyl isothiocyanate (1.53 g, 15.42 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (8.24 g, 19.45 mmol) and pyridine (55 mL) were used according to general procedure I. The product was recrystallized from 1,4-dioxane to afford 3.29 g (83%) of a white solid. MS (CI): m/z 274. Anal. Calcd for C10H8Cl3N3-(0.6 C4H8O2): C, 45.21; H, 3.92; N, 12.76. Found: C, 45.37; H, 3.91; N, 12.76.

Workup

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

Sources & evidence

ORD record
ord-f2335d1862ea49dfaee8d52e84d4de56
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06204249B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes