Benzocaine → Ethyl 4-[(pentadecafluoroheptyl)methylamino]benzoate

HRID 2058750Notes

Reaction equation

HRID 2058750 reaction equation
[F:1][C:2]([F:31])([C:27]([F:30])([F:29])[F:28])[C:3]([F:26])([F:25])[C:4]([F:24])([F:23])[C:5]([F:22])([F:21])[C:6]([F:20])([F:19])[C:7](COS(C(F)(F)F)(=O)=O)([F:9])[F:8].[NH2:32][C:33]1[CH:43]=[CH:42][C:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:35][CH:34]=1.[CH3:44]N(C)P(N(C)C)(N(C)C)=O>O>[F:1][C:2]([F:31])([C:27]([F:28])([F:29])[F:30])[C:3]([F:25])([F:26])[C:4]([F:23])([F:24])[C:5]([F:21])([F:22])[C:6]([F:20])([F:19])[C:7]([N:32]([CH3:44])[C:33]1[CH:34]=[CH:35][C:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:42][CH:43]=1)([F:8])[F:9]

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 110169092,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluorooctyl trifluoromethanesulfonate

Product 1

HCID 54405524Ethyl 4-[(pentadecafluoroheptyl)methylamino]benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 45 g. of (pentadecafluoroheptyl)(trifluoromethanesulfonyloxy)methane and 28 g. of ethyl 4-aminobenzoate in 50 ml. of hexamethylphosphoramide is stirred at 120° C. for 72 hours, diluted with water, and filtered. A methylene chloride solution of the solid is dried over anhydrous magnesium sulfate and evaporated. The residue is recrystallized from acetonitrile to yield the product as a white solid.

Workup

  1. filtrationfiltered
  2. dry with materialA methylene chloride solution of the solid is dried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe residue is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-d18cf454f32b46e887ab6b56212c61b6
Source dataset
uspto-grants-1982_03
Patent number
US04318914

Reaction notes

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