Benzocaine → Ethyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

HRID 652018Notes

Reaction equation

HRID 652018 reaction equation
CS(OO[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])(=O)=O.[NH2:25][C:26]1[CH:36]=[CH:35][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=1>CN(C)P(N(C)C)(N(C)C)=O>[CH3:22][Si:21]([CH3:24])([CH3:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][NH:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 2019829214-(Trimethylsilyl)tetradecyloxy methanesulfonate

Product 1

HCID 13884860Ethyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 20.8 g. 14-(trimethylsilyl)tetradecyloxy methanesulfonate and 20 g. ethyl 4-aminobenzoate in 50 ml. hexamethylphosphoramide was stirred at 110° for 18 hr. The reaction was diluted with 100 ml. water and extracted three times with 150 ml. portions of methylene chloride. The combined organic layers were washed with brine, dried with anhydrous magnesium sulfate, passed through a pad of hydrous magnesium silicate, and evaporated. The residue was crystallized from 250 ml. ethanol to yield the title compound as a crystalline solid, m.p. 91°-92° C.

Workup

  1. additionThe reaction was diluted with 100 ml
  2. extractionwater and extracted three times with 150 ml
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was crystallized from 250 ml

Sources & evidence

ORD record
ord-ea9ce114140c48708ead8eab695b9ef5
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Reaction notes

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