Benzocaine → HCID 22225233, compound

HRID 1744802Notes

Reaction equation

HRID 1744802 reaction equation
[CH3:1][C:2]1[C:3]2[CH:15]=[CH:14][C:13](=[O:16])[N:12]([C:17]3[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:19][CH:18]=3)[C:4]=2[N:5]=[C:6](S(C)(=O)=O)[N:7]=1.[NH2:30][C:31]1[CH:41]=[CH:40][C:34]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:33][CH:32]=1>O1CCOCC1>[CH2:38]([O:37][C:35]([C:34]1[CH:40]=[CH:41][C:31]([NH:30][C:6]2[N:7]=[C:2]([CH3:1])[C:3]3[CH:15]=[CH:14][C:13](=[O:16])[N:12]([C:17]4[CH:18]=[CH:19][C:20]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])=[CH:28][CH:29]=4)[C:4]=3[N:5]=2)=[CH:32][CH:33]=1)=[O:36])[CH3:39]

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 10070446HCID 10070446, compound

Product 1

HCID 22225233HCID 22225233, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of compound 2 (0.5 g; 1.2 mmol) and ethyl p-aminobenzoate (1 g; 6 mmol) in 10 mL of dioxane was refluxed under stirring for 14 h. The reaction mixture was concentrated, purified by silica gel column chromatography (eluant: n-hexane/ethyl acetate=1/1 to 1/2) to yield compound 3 (0.38 g; 63%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by silica gel column chromatography (eluant: n-hexane/ethyl acetate=1/1 to 1/2)

Sources & evidence

ORD record
ord-2459f2a34fa547f5ac64ab60fa9a723b
Source dataset
uspto-grants-2006_03
Patent number
US07019002B2

Reaction notes

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