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

HRID 2163784Notes

Reaction equation

HRID 2163784 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-cd871ec3d9964994a250f236be6e1256
Source dataset
uspto-grants-1979_01
Patent number
US04136256

Reaction notes

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