Benzocaine → HCID 23468284, compound

HRID 443633Notes

Reaction equation

HRID 443633 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 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 23468302HCID 23468302, compound

Product 1

HCID 23468284HCID 23468284, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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, m.p. 109°-110° C.

Workup

  1. temperatureThe solution is cooled
  2. filtrationfiltered
  3. washthe solid washed with ethanol and water
  4. customto give 7.7 g
  5. customRecrystallization from ethanol
  6. customonce from acetone-hexane gives crystals, m.p. 109°-110° C.

Sources & evidence

ORD record
ord-e0f0c62c961b43cd96175d848945cbf8
Source dataset
uspto-grants-1981_04
Patent number
US04260816

Reaction notes

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