Benzocaine → HCID 23457874, compound

HRID 1680297Notes

Reaction equation

HRID 1680297 reaction equation
[CH3:1][CH:2]([CH2:5][CH:6]([CH3:14])[CH2:7][CH:8]([CH3:13])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:3]Br.[NH2:15][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1>>[CH3:1][CH:2]([CH2:5][CH:6]([CH3:14])[CH2:7][CH:8]([CH3:13])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:3][NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 2337BenzocaineHCID 23457764HCID 23457764, compound

Product 1

HCID 23457874HCID 23457874, compound

Conditions

Temperature
120 °C

Procedure

A solution of 9 g. (34.2 m moles) 2,4,6,8-tetramethylnonylbromide, 6 g. (1.06 eq) ethyl 4-aminobenzoate, and 5 g. (1.05 eq) dry, powdered potassium carbonate in 50 ml. hexamethylphosphoramide is stirred at 120° C. for 17 hours. The cooled solution is diluted with 100 ml. water, the precipitate is filtered and washed with 100 ml. 50% aqueous ethanol. The product is dried and crystallized twice from ethanol to colorless crystals.

Workup

  1. custom(1.05 eq) dry
  2. additionThe cooled solution is diluted with 100 ml
  3. filtrationwater, the precipitate is filtered
  4. washwashed with 100 ml
  5. customThe product is dried
  6. customcrystallized twice from ethanol to colorless crystals

Sources & evidence

ORD record
ord-d23777a8a74d44a2a7eece1f8e2e5a8d
Source dataset
uspto-grants-1981_06
Patent number
US04272546

Reaction notes

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