Benzocaine → HCID 20378381, compound

HRID 2051911Notes

Reaction equation

HRID 2051911 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.CN(C)P(N(C)C)(N(C)C)=O.Br[CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O>[O:27]([CH2:26][CH2:25][NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 68526Benzene, (2-bromoethoxy)-

Product 1

HCID 20378381HCID 20378381, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 33 g of ethyl p-aminobenzoate, 80 ml of hexamethylphosphoramide and 20.1 g of β-bromophenetole is heated at 110° C. for 20 hours. The mixture is cooled, diluted with 25 ml of water, chilled, filtered and the solid washed with ethanol and with water to give crystals, mp 126°-129° C. Recrystallization from ethanol gives pale yellow crystals, mp 129°-131° C.

Workup

  1. temperatureThe mixture is cooled
  2. temperaturechilled
  3. filtrationfiltered
  4. washthe solid washed with ethanol and with water
  5. customto give crystals, mp 126°-129° C
  6. customRecrystallization from ethanol
  7. customgives pale yellow crystals, mp 129°-131° C.

Sources & evidence

ORD record
ord-7ac1ae2d14734c9f8dfc8d5f3e7ea411
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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