Benzocaine → Ethyl p-{[2-(2-naphthyloxy)ethyl]amino}benzoate

HRID 443637Notes

Reaction equation

HRID 443637 reaction equation
CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)(=O)=O.[NH2:19][C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1.CN(C)P(N(C)C)(N(C)C)=O>O>[CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[O:8][CH2:7][CH2:6][NH:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 190043832-(2-Naphthyloxy)ethyl methanesulfonate

Product 1

HCID 23468273Ethyl p-{[2-(2-naphthyloxy)ethyl]amino}benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 18.7 g. of 2-(2-naphthyloxy)ethanol O-methanesulfonate and 23.6 g. of ethyl p-aminobenzoate is heated in 300 ml. of hexamethylphosphoramide at 110° C. for 16 hours. The mixture is cooled, diluted with water and worked up as described in Example 3 to give the crystalline product. Recrystallization from ethanol gives crystals, m.p. 158°-162° C.

Workup

  1. additionA mixture of 18.7 g
  2. temperatureThe mixture is cooled
  3. customto give the crystalline product
  4. customRecrystallization from ethanol
  5. customgives crystals, m.p. 158°-162° C.

Sources & evidence

ORD record
ord-50cbeef0289e48c89837662bb5fdca32
Source dataset
uspto-grants-1981_04
Patent number
US04260816

Reaction notes

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