Benzocaine → HCID 20378377, compound

HRID 2051908Notes

Reaction equation

HRID 2051908 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22]Br)=[CH:16][CH:15]=1.CN(C)P(N(C)C)(N(C)C)=O>O>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 877972-Bromoethyl p-bromophenyl ether

Product 1

HCID 20378377HCID 20378377, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 26.4 g of ethyl p-aminobenzoate, 22.4 g of 2-bromoethyl p-bromophenyl ether and 80 ml of hexamethylphosphoramide is heated at 100°-110° C. for 20 hours. The mixture is chilled, diluted with 25 ml of water, chilled and filtered. The solid is washed with 100 ml of ethanol-water (1:1), with 25 ml of ethanol and with water to give tan crystals, mp 128°-133° C. Recrystallization from ethanol gives yellow crystals, mp 135.5°-137° C.

Workup

  1. temperatureis heated at 100°-110° C. for 20 hours
  2. temperatureThe mixture is chilled
  3. temperaturechilled
  4. filtrationfiltered
  5. washThe solid is washed with 100 ml of ethanol-water (1:1), with 25 ml of ethanol and with water
  6. customto give tan crystals, mp 128°-133° C
  7. customRecrystallization from ethanol
  8. customgives yellow crystals, mp 135.5°-137° C.

Sources & evidence

ORD record
ord-f93c672d32d64162ba91dcc243be1fd0
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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