Triethylamine → HCID 67344602, compound

HRID 1673392Notes

Reaction equation

HRID 1673392 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](Cl)=[O:13].[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(Cl)Cl>[Br:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([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

6

Reactant 4

HCID 8471TriethylamineHCID 74377Benzoyl chloride, 3-bromo-HCID 516892Sodium BicarbonateHCID 58508592Tert-butyl 2-amino-4-phenoxybenzoate

Product 1

HCID 67344602HCID 67344602, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.056 mL of triethylamine and 0.029 mL of 3-bromobenzoyl chloride were added to 3.0 mL of methylene chloride solution containing 57 mg of tert-butyl 2-amino-4-phenoxybenzoate at room temperature sequentially and stirred at the same temperature for 1 hour. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture. 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-(3-bromobenzamido)-4-phenoxybenzoate.

Workup

  1. customThe organic layer was separated
  2. customthe solvent was evaporated under reduced pressure
  3. 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-70d0064668f64654807ae3044a49ee0b
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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