Benzocaine → HCID 20482520, compound

HRID 1106144Notes

Reaction equation

HRID 1106144 reaction equation
[O:1]=[C:2]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]Br.[NH2:19][C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1.CN(C)P(N(C)C)(N(C)C)=O>O>[O:1]=[C:2]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 20482581HCID 20482581, compound

Product 1

HCID 20482520HCID 20482520, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 15 g. of 6-oxohexadecyl bromide and 15.6 g. of ethyl 4-aminobenzoate in 60 ml. of hexamethylphosphoramide is stirred at 120° C. for 18 hours, allowed to cool, and diluted with water. The mixture is filtered and the resulting solid is dissolved in methylene chloride. The solution is washed with diluted hydrochloric acid, dried, and evaporated to yield a brown solid. Crystallization from ethanol yields ethyl 4-(6-oxohexadecylamino)benzoate as a white solid.

Workup

  1. temperatureto cool
  2. filtrationThe mixture is filtered
  3. dissolutionthe resulting solid is dissolved in methylene chloride
  4. washThe solution is washed with diluted hydrochloric acid
  5. customdried
  6. customevaporated
  7. customto yield a brown solid
  8. customCrystallization from ethanol

Sources & evidence

ORD record
ord-341019a3946f4c3e9d848d600b264ac4
Source dataset
uspto-grants-1982_01
Patent number
US04311846

Reaction notes

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