Hydrochloric Acid → Ethyl 4-(2-sulfoethylamino)benzoate

HRID 904248Notes

Reaction equation

HRID 904248 reaction equation
Br[CH2:2][CH2:3][S:4]([O-:7])(=[O:6])=[O:5].[Na+].[NH2:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1.Cl>CN(C)P(N(C)C)(N(C)C)=O>[S:4]([CH2:3][CH2:2][NH:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:19][CH:20]=1)([OH:7])(=[O:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2337BenzocaineHCID 236667972-Bromoethanesulfonic acid, sodium salt

Product 1

HCID 21163340Ethyl 4-(2-sulfoethylamino)benzoate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 4.1 g. of sodium 2-bromoethanesulfonate and 7.9 g. of ethyl 4-aminobenzoate in 110 ml. of hexamethylphosphoramide is stirred at 125° for 18 hours and then poured into dilute hydrochloric acid. The solid is collected by filtration, dried and recrystallized from acetonitrile to yield ethyl 4-(2-sulfoethylamino)benzoate as a white solid.

Workup

  1. filtrationThe solid is collected by filtration
  2. customdried
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-82821c4028e342f7b5df3fc65f2496f2
Source dataset
uspto-grants-1980_10
Patent number
US04230628

Reaction notes

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