Benzocaine → HCID 86745779, compound

HRID 1195925Notes

Reaction equation

HRID 1195925 reaction equation
CN(C=O)C.[C:6]([C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1)([O:8][CH2:9][CH3:10])=[O:7].[CH:18]([S:20]([F:23])(=[O:22])=[O:21])=[CH2:19]>O>[C:6]([C:11]1[CH:12]=[CH:13][C:14]([NH:15][CH:19]=[CH:18][S:20]([F:23])(=[O:22])=[O:21])=[CH:16][CH:17]=1)([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 6228DimethylformamideHCID 69612Ethenesulfonyl fluoride

Product 1

HCID 86745779HCID 86745779, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a 75 mL DMF solution of 4-carboethoxyaniline (3.88 g, 23.5 mmol) was added ethenesulfonyl fluoride (3.3 mL, 30 mmol) under nitrogen. The solution was warmed to 100-120° C. for 6 hours. The cooled solution was slowly Poured into water and chilled in ice. The yellow solid precipitate was collected, dissolved in methylene chloride, washed with brine and dried (Na2SO4). After the solvent had been removed by distillation, the brown solid (5.4 g) was crystallized from methylene chloride/ether/hexane. The title compound (3.2 g, 49% yield) was obtained as a tan solid, mp 109.5°-111.5° C.

Workup

  1. temperaturechilled in ice
  2. customThe yellow solid precipitate was collected
  3. dissolutiondissolved in methylene chloride
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customAfter the solvent had been removed by distillation
  7. customthe brown solid (5.4 g) was crystallized from methylene chloride/ether/hexane

Sources & evidence

ORD record
ord-659094e313744b2bad3958053ee81b08
Source dataset
uspto-grants-1992_05
Patent number
US05112866

Reaction notes

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