Benzocaine → HCID 20475786, compound

HRID 905267Notes

Reaction equation

HRID 905267 reaction equation
CS(O[CH2:6][CH2:7][CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)(=O)=O.[NH2:13][C:14]1[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=1>CN(C)P(N(C)C)(N(C)C)=O>[CH:8]1([CH2:7][CH2:6][NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:23][CH:24]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 15343325HCID 15343325, compound

Product 1

HCID 20475786HCID 20475786, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 5 g. of 2-cyclopentylethyl methanesulfonate and 8.59 g. of ethyl p-aminobenzoate in 30 ml. of hexamethylphosphoramide is stirred at 110° C. under argon atmosphere for 18 hours. The cooled solution is diluted with 30 ml. of water and the resulting tan solid is collected by filtration. Recrystallization from ethanol-water furnishes ethyl p-[2-(cyclopentyl)ethyl]aminobenzoate as off-white crystals.

Workup

  1. additionThe cooled solution is diluted with 30 ml
  2. filtrationof water and the resulting tan solid is collected by filtration
  3. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-9f974d9595f345018ae9c8994b658b78
Source dataset
uspto-grants-1983_12
Patent number
US04423051

Reaction notes

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