Hydrochloric Acid → HCID 57879406, compound

HRID 1673337Notes

Reaction equation

HRID 1673337 reaction equation
C(=O)([O-])[O-].[K+].[K+].S([O:12][CH3:13])(OC)(=O)=O.[C:14]([NH:22][C:23]1[CH:31]=[C:30]([I:32])[CH:29]=[CH:28][C:24]=1[C:25](O)=[O:26])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>C(OCC)(=O)C.CN(C)C=O>[C:14]([NH:22][C:23]1[CH:31]=[C:30]([I:32])[CH:29]=[CH:28][C:24]=1[C:25]([O:12][CH3:13])=[O:26])(=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 57879422HCID 57879422, compound

Product 1

HCID 57879406HCID 57879406, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.62 g of potassium carbonate and 0.43 ml of dimethyl sulfate were added to 15 mL of N,N-dimethylformamide solution containing 1.5 g of 2-(benzamido)-4-iodobenzoic acid at room temperature and stirred at the same temperature for 1 hour. Ethyl acetate and 1.0 mol/L hydrochloric acid were added to the reaction mixture. The organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residual was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to obtain 1.3 g of methyl 2-(benzamido)-4-iodobenzoate as white solid.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residual was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]

Sources & evidence

ORD record
ord-b506fe9c72b743978faa69274ab8c7c2
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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