Methyl iodide → Benzoic Acid

HRID 13490

Reaction equation

HRID 13490 reaction equation
NC1C=C(C=CC=1NC)OC1C=CN=C(C(NC)=O)C=1.N([C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1)=C=S.IC>CO>[C:28]([OH:30])(=[O:29])[C:27]1[CH:31]=[CH:32][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2429464-Isothiocyanatobenzoic acidHCID 177558384-(3-Amino-4-methylamino-phenoxy)-pyridine-2-carboxylic acid methylamide

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 4-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 4-({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-0db3fcedba7b4eb1b027317ca6693d87
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Linked notes

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