3,5-Dichlorobenzoic acid → Tert-butyl 2-(3,5-dichlorobenzamido)-4-phenethylbenzoate

HRID 1673520Notes

Reaction equation

HRID 1673520 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([Cl:17])[CH:16]=1)[C:11]([OH:13])=O.[NH2:18][C:19]1[CH:31]=[C:30]([CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=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>[Cl:17][C:15]1[CH:14]=[C:10]([CH:9]=[C:8]([Cl:7])[CH:16]=1)[C:11]([NH:18][C:19]1[CH:31]=[C:30]([CH2:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:29]=[CH:28][C:20]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:13]

Participants

8

Reactant 4

HCID 58113,5-Dichlorobenzoic acidHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 58508624Tert-butyl 2-amino-4-phenethylbenzoate

Product 1

HCID 67342900Tert-butyl 2-(3,5-dichlorobenzamido)-4-phenethylbenzoate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

2.0 mL of methylene chloride, 2.7 μL of N,N-dimethylformamide and 0.061 mL of oxalyl chloride were sequentially added to 0.13 g of 3,5-dichlorobenzoic acid at room temperature and stirred at the same temperature for 1 hour. The reaction mixture was added to a mixed solution of 3.0 mL of methylene chloride and 0.45 mL of triethylamine containing 60 mg of tert-butyl 2-amino-4-phenethylbenzoate at room temperature and stirred at the same 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-(3,5-dichlorobenzamido)-4-phenethylbenzoate.

Workup

  1. stirringstirred at the same 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-4dbaf320b1dc486b98babda8f138e594
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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