Benzocaine → Ethyl 4-(13,13-dimethyltetradecyl)aminobenzoate

HRID 1980185Notes

Reaction equation

HRID 1980185 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]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][C:2]([CH3:17])([CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][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 2043733913,13-Dimethyltetradecyl bromide

Product 1

HCID 20437372Ethyl 4-(13,13-dimethyltetradecyl)aminobenzoate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 10 g. of 13,13-dimethyltetradecyl bromide and 10.8 g. of ethyl 4-aminobenzoate in 75 ml. hexamethylphosphoramide is heated at 110° C. for 17 hours. The cooled solution is diluted with 100 ml. water, filtered, and the residue is washed in portions with 100 ml. 50% ethanol-water. After drying, the product is crystallized from ethanol to yield ethyl 4-(13,13-dimethyltetradecyl)aminobenzoate as colorless crystals.

Workup

  1. additionThe cooled solution is diluted with 100 ml
  2. filtrationwater, filtered
  3. washthe residue is washed in portions with 100 ml
  4. customAfter drying
  5. customthe product is crystallized from ethanol

Sources & evidence

ORD record
ord-2ae954eea59f4473aa7be10e7001a325
Source dataset
uspto-grants-1984_11
Patent number
US04485105

Reaction notes

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