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

HRID 1105892Notes

Reaction equation

HRID 1105892 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-122017a5a0da47d39380e5eaadfa02e7
Source dataset
uspto-grants-1982_01
Patent number
US04310545

Reaction notes

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