O-Phenylenediamine → HCID 178420008, compound

HRID 2064595Notes

Reaction equation

HRID 2064595 reaction equation
C(NC([C:8]1[CH:25]=[CH:24][C:11]2[NH:12][C:13]([C:15]3[C:23]4[C:18](=CC=CC=4)[NH:17][N:16]=3)=[N:14][C:10]=2[CH:9]=1)=O)C(C)C.C1(N)C=CC=CC=1N.S(=O)(O)[O-].[Na+]>CN(C)C=O>[NH:17]1[CH:18]=[CH:23][C:15]([C:13]2[NH:12][C:11]3[CH:24]=[CH:25][CH:8]=[CH:9][C:10]=3[N:14]=2)=[N:16]1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 23665763Sodium BisulfiteHCID 178449281HCID 178449281, compound

Product 1

HCID 178420008HCID 178420008, compoundYield 121.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1H-pyrazole-3-carbaldehyde (0.961 g, Reference Example 10), o-phenylenediamine (0.973 g), sodium bisulfite (1.898 g) and dry dimethylformamide (10 mL) was stirred at reflux for 2 hours, then cooled to room temperature and then poured onto cracked ice (35 g). The mixture was filtered and the solid was washed with aqueous sodium bicarbonate and then with water. The solid was vacuum dried at 70° C. and then recrystallised from ethanol to give 2-(1H-pyrazol-3yl)-1H-benzoimidazole (0.645 g) as a pale yellowish solid, mp 335-338° C. [Elemental analysis:—C, 62.56%; H, 4.04%; N, 29.14%. Calculated for C10H8N4:—C, 65.19%; H, 4.39%; N, 30.42%].

Workup

  1. temperatureat reflux for 2 hours
  2. additionpoured
  3. filtrationThe mixture was filtered
  4. washthe solid was washed with aqueous sodium bicarbonate
  5. customdried at 70° C.
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-122f71e95b1f44f292c88fefca013800
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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