Methyl iodide → Benzoic Acid

HRID 2070293Notes

Reaction equation

HRID 2070293 reaction equation
CNC=O.N([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([OH:13])=[O:12])=C=S.IC>CO>[C:11]([OH:13])(=[O:12])[C:10]1[CH:14]=[CH:15][CH:16]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 31254N-MethylformamideHCID 75046Benzoic acid, 3-isothiocyanato-

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To 4-[3-amino-4-(methylamino) phenoxy](2-pyridyl)}-N-methylcarboxamide (1 eq) in methanol was added 3-isothiocyanatobenzoic acid (1 eq) and stirred at 60° C. for 3 h. To it was then added iodomethane (1 eq) and heated to 60° C. for 3 h and concentrated the solvent and purified on silica gel to yield 3-({1-methyl-5-[2-(N-methylcarbamoyl)(4-pyridyloxy))]benzimidazol-2-yl}amino)benzoic acid. MS: MH+=417.

Workup

  1. concentrationconcentrated the solvent
  2. custompurified on silica gel

Sources & evidence

ORD record
ord-07c53af854d640e996e9238fa915662f
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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