Benzocaine → Ethyl 4-(14-methylpentadecyl)aminobenzoate

HRID 2163781Notes

Reaction equation

HRID 2163781 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-3b55739531184c97900765658aba7645
Source dataset
uspto-grants-1979_01
Patent number
US04136256

Reaction notes

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