Benzocaine → Ethyl 4-[2-benzyloxy-5-bromophenylacetamido]benzoate

HRID 355809Notes

Reaction equation

HRID 355809 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH2:16][C:17]([OH:19])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[NH2:24][C:25]1[CH:35]=[CH:34][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][CH:26]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C=O)C.ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH2:16][C:17]([NH:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:34][CH:35]=1)=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 2337BenzocaineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 33070112-[2-(Benzyloxy)-5-bromophenyl]acetic acid

Product 1

HCID 54475189Ethyl 4-[2-benzyloxy-5-bromophenylacetamido]benzoateYield 42.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-benzyloxy-5-bromophenylacetic acid (3.2 g) in toluene (100 ml) was added thionyl chloride (1.0 ml) and DMF (3 drops ). The reaction was stirred at 80° C. for 1 hour and cooled to ambient temperature. ethyl 4-aminobenzoate (2.0 g) and triethylamine (2 ml) were added to the reaction mixture with stirring. After standing for 18 hours, the mixture was diluted with dichloromethane and washed with water, 1N HCl solution, water and sautrated aqueous NaHCO3 solution. The organic extract was dried (MgSO4), filtered and evaporated and the residue purified by trituration with diethyl ether to give ethyl 4-[2-benzyloxy-5-bromophenylacetamido]benzoate (2.0 g) mpt. 174°-176° C.

Workup

  1. temperaturecooled to ambient temperature
  2. stirringwith stirring
  3. waitAfter standing for 18 hours
  4. washwashed with water, 1N HCl solution, water
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customthe residue purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-99db7a75acb44c3f8d1d80065c95b309
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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