1,2-Dichloroethane → HCID 178526862, compound

HRID 1012050Notes

Reaction equation

HRID 1012050 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].NC1C(C(O)=[O:16])=NNC=1.C(Cl)CCl.C1C=[CH:24][C:25]2[N:30]([OH:31])[N:29]=[N:28][C:26]=2[CH:27]=1>CN(C=O)C.CC(O)=O>[N+:30]([C:25]1[C:26]([C:27]2[NH:8][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[N:7]=2)=[N:28][NH:29][CH:24]=1)([O-:31])=[O:16]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 7243O-PhenylenediamineHCID 757711-HydroxybenzotriazoleHCID 178508058HCID 178508058, compound

Product 1

HCID 178526862HCID 178526862, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of o-phenylenediamine (1.51 g, 14.0 mmol), 4-amino-1H-pyrazole-3-carboxylic acid (2.00 g, 12.7 mmol), EDC (2.93 g, 15.3 mmol) and HOBt (2.08 g, 15.3 mmol) in DMF (70 ml) was stirred at ambient temperature for 24 h. The mixture was reduced in vacuo and the residue dissolved in AcOH (150 ml) and heated at reflux for 3 h. The solvent was removed in vacuo, water (100 ml) added and the resultant solid collected by filtration washing with water. The solid was dried through azeotrope with toluene (3×150 ml) yielding 2-(4-nitro-1H-pyrazol-3-yl)-1H-benzimidazole as a yellow solid (1.44 g, 50%). A 100 mg portion was purified by preparative LC/MS and following evaporation of product containing fractions gave 70 mg of the title compound. (LC/MS: Rt 1.72, [M+H]+ 229.61).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customThe solvent was removed in vacuo, water (100 ml)
  4. additionadded
  5. filtrationthe resultant solid collected by filtration
  6. washwashing with water
  7. dry with materialThe solid was dried through azeotrope with toluene (3×150 ml)

Sources & evidence

ORD record
ord-c30927e576d94f5c85d8f1ad2433252d
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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