Pyridinium chloride → 2-methyl-7-trifluoromethyl-3H-benzimidazol-5-ol

HRID 1846515Notes

Reaction equation

HRID 1846515 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:13]([F:16])([F:15])[F:14])[C:6]2[N:10]=[C:9]([CH3:11])[NH:8][C:7]=2[CH:12]=1.Cl.N1C=CC=CC=1>CN(C=O)C>[CH3:11][C:9]1[NH:8][C:7]2[CH:12]=[C:3]([OH:2])[CH:4]=[C:5]([C:13]([F:16])([F:14])[F:15])[C:6]=2[N:10]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 669782136-methoxy-2-methyl-4-trifluoromethyl-1H-benzimidazole

Product 1

HCID 669782592-methyl-7-trifluoromethyl-3H-benzimidazol-5-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A well stirred mixture of 450 mg (1.95 mmol) 6-methoxy-2-methyl-4-trifluoromethyl-1H-benzimidazole and 2.50 g (21.6 mmol) pyridine hydrochloride was heated for 15 min to 200° C. After cooling to RT the reaction mixture was combined with 3.0 mL DMF and purified by preparative HPLC. The fractions containing product were combined and evaporated down i.vac.

Workup

  1. temperaturewas heated for 15 min to 200° C
  2. custompurified by preparative HPLC
  3. additionThe fractions containing product
  4. customevaporated down i.vac

Sources & evidence

ORD record
ord-68c0fe24adfa46c5894f204c1205570c
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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