2-Methoxybenzoic acid → HCID 67342584, compound

HRID 1673522Notes

Reaction equation

HRID 1673522 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O.[NH2:18][C:19]1[CH:31]=[C:30]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:29]=[CH:28][C:20]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(=O)([O-])O.[Na+]>C(N(CC)CC)C.C(Cl)Cl.CN(C)C=O>[CH3:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH:18][C:19]1[CH:31]=[C:30]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:29]=[CH:28][C:20]=1[C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])=[O:13]

Participants

8

Reactant 4

HCID 113702-Methoxybenzoic acidHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 58508592Tert-butyl 2-amino-4-phenoxybenzoate

Product 1

HCID 67342584HCID 67342584, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

1.0 mL of methylene chloride, 2.7 pit of N,N-dimethylformamide and 0.061 mL of oxalyl chloride were added to 0.11 g of 2-methoxybenzoic acid at room temperature sequentially and stirred at the same temperature for 1 hour. The reaction mixture was added to a mixed solution of 4.0 mL of methylene chloride and 0.45 mL triethylamine containing 57 mg of tert-butyl 2-amino-4-phenoxybenzoate and stirred at room temperature for 1 hour. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the organic layer was separated, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=4:1] to obtain tert-butyl 2-(2-methoxybenzamido)-4-phenoxybenzoate.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. customthe organic layer was separated
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=4:1]

Sources & evidence

ORD record
ord-80100f48257843669cd3acdc1c3b85a5
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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