Benzocaine → HCID 53818253, compound

HRID 569458Notes

Reaction equation

HRID 569458 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH3:2].[CH2:13]([CH:19]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:20](Cl)=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>N1C=CC=CC=1.C(#N)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:20](=[O:21])[CH:19]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 2337BenzocaineHCID 11437295Isopalmitic chloride

Product 1

HCID 53818253HCID 53818253, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Procedure

In a mixture of 40 ml of pyridine and 300 ml of acetonitrile was dissolved 82.5 g of 4-aminobenzoic acid ethyl ester and then 137.5 g of 2-hexyldecanoyl chloride was added dropwise to the solution thus formed at room temperature over a period of about 30 minutes. Thereafter, after keeping the mixture at 50° C. for 2 hours, the reaction mixture was allowed to cool and extracted with a mixture of ethyl acetate and an aqueous hydrochloric acid solution. The extract thus obtained was dried by magnesium sulfate and concentrated to provide 188 g of oily 4-(2-hexyldecanamido)benzoic acid ethyl ester.

Workup

  1. customthus formed at room temperature over a period of about 30 minutes
  2. customat 50° C.
  3. customfor 2 hours
  4. temperatureto cool
  5. extractionextracted with a mixture of ethyl acetate
  6. extractionThe extract thus
  7. customobtained
  8. dry with materialwas dried by magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5fc9a517c79e4d52bed7b91eb9c7e5ff
Source dataset
uspto-grants-1988_03
Patent number
US04732845

Reaction notes

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