Benzocaine → HCID 57683229, compound

HRID 1864962Notes

Reaction equation

HRID 1864962 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH3:2].C(N(CC)CC)C.[F:20][C:21]([F:38])([F:37])[C:22]1[CH:27]=[CH:26][C:25]([C:28]2[C:29]([C:34](Cl)=[O:35])=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:24][CH:23]=1.FC(F)(F)C1C=CC(C2C(C(O)=O)=CC=CC=2)=CC=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:34]([C:29]2[C:28]([C:25]3[CH:26]=[CH:27][C:22]([C:21]([F:20])([F:37])[F:38])=[CH:23][CH:24]=3)=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:35])=[CH:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 2337BenzocaineHCID 8471TriethylamineHCID 552514'-(Trifluoromethyl)(1,1'-biphenyl)-2-carboxylic acidHCID 110660004'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chloride

Product 1

HCID 57683229HCID 57683229, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

4-Aminobenzoic acid ethyl ester (0.568 g) and triethylamine (0.570 g) were dissolved in methylene chloride (20 mL), and to this solution was dropwise added a solution of 4′-trifluoromethylbiphenyl-2-carboxylic acid chloride, which is prepared from 4′-trifluoromethylbiphenyl-2-carboxylic acid (1.00 g) in a similar manner to Example 1d), in methylene chloride under ice-cooling. The solution was stirred at room temperature for 2 hours, followed by addition of methylene chloride (100 mL). The reaction mixture was washed with 2N hydrochloric acid and saturated brine, dried over sodium sulfate and concentrated to give the title compound (1.43 g).

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed with 2N hydrochloric acid and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cecaaf75d3a44d0a99f2859d0abf9bc8
Source dataset
uspto-grants-2009_12
Patent number
US07625948B2

Reaction notes

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