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

HRID 1395709Notes

Reaction equation

HRID 1395709 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-c1146cc34e54497699223d24f0a7faf4
Source dataset
uspto-grants-1980_05
Patent number
US04205085

Reaction notes

Loading…