Benzocaine → HCID 21318765, compound

HRID 262929Notes

Reaction equation

HRID 262929 reaction equation
[O:1]=[C:2]([CH2:14][CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]Br.[NH2:21][C:22]1[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=1>CN(C)P(N(C)C)(N(C)C)=O>[O:1]=[C:2]([CH2:14][CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 21318800HCID 21318800, compound

Product 1

HCID 21318765HCID 21318765, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 15 g. (43.2 mmoles) 11-oxo-15,15-dimethylhexadecyl bromide and 14.3 g. (2 eq.) ethyl 4-aminobenzoate in 100 ml. hexamethylphosphoramide is heated at 120° C. for 18 hours. The cooled solution is diluted with 200 ml. water and filtered. The resultant solid is washed in portions with 200 ml. 50% ethanol-water, dried, and crystallized from ethanol to yield a colorless, waxy solid.

Workup

  1. additionThe cooled solution is diluted with 200 ml
  2. filtrationwater and filtered
  3. washThe resultant solid is washed in portions with 200 ml
  4. dry with material50% ethanol-water, dried
  5. customcrystallized from ethanol
  6. customto yield a colorless, waxy solid

Sources & evidence

ORD record
ord-6a31b05107de4e29b25b1a894929e9b8
Source dataset
uspto-grants-1979_05
Patent number
US04154756

Reaction notes

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