Benzocaine → Ethyl 4-(14-methylpentadecyl)aminobenzoate

HRID 1733525Notes

Reaction equation

HRID 1733525 reaction equation
[CH3:1][CH:2]([CH3:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.[NH2:18][C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1>CN(C)P(N(C)C)(N(C)C)=O>[CH3:1][CH:2]([CH3:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 10881292Pentadecane, 1-bromo-14-methyl-

Product 1

HCID 20437387Ethyl 4-(14-methylpentadecyl)aminobenzoate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 10 g. of 14-methylpentadecyl bromide and 10.8 g. of ethyl 4-aminobenzoate in 75 ml. hexamethylphosphoramide is heated at 120° C. for 17 hours. The cooled solution is diluted with 100 ml. water, filtered, and the residue is washed with 100 ml. 50% ethanol-water. The product is dried, then crystallized from ethanol to yield ethyl 4-(14-methylpentadecyl)aminobenzoate as colorless crystals.

Workup

  1. additionThe cooled solution is diluted with 100 ml
  2. filtrationwater, filtered
  3. washthe residue is washed with 100 ml
  4. customThe product is dried
  5. customcrystallized from ethanol

Sources & evidence

ORD record
ord-f520a3cad9cf4d91b22081b92fde2a0e
Source dataset
uspto-grants-1980_12
Patent number
US04242273

Reaction notes

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