Benzocaine → HCID 23468284, compound

HRID 2051889Notes

Reaction equation

HRID 2051889 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1)(=O)=O.[NH2:23][C:24]1[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=1>CN(C)P(N(C)C)(N(C)C)=O.O>[CH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][NH:23][C:24]1[CH:25]=[CH:26][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 2337BenzocaineHCID 23468302HCID 23468302, compound

Product 1

HCID 23468284HCID 23468284, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 10.0 g of 6-(2-naphthyloxy)-1-hexanol O-methanesulfonate and 9.7 g of ethyl 4-aminobenzoate in 50 ml of hexamethylphosphoramide is heated at 110° C. for 16 hours. The solution is cooled, diluted with water, filtered and the solid washed with ethanol and water to give 7.7 g of product. Recrystallization from ethanol and once from acetone-hexane gives crystals, mp 109°-110° C.

Workup

  1. temperatureThe solution is cooled
  2. filtrationfiltered
  3. washthe solid washed with ethanol and water

Sources & evidence

ORD record
ord-bd433c6b5bfe43998491d3401bfff6ef
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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