O-Phenylenediamine → HCID 178420008, compound

HRID 2182356Notes

Reaction equation

HRID 2182356 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%]. (b) 3-(5,6-Dimethyl-1H-benzoimidazol-2-yl)-5-methoxy-1H-indazole

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-be400f46294645d682cad16a789ee7d8
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

Loading…