Benzocaine → HCID 20378391, compound

HRID 2051913Notes

Reaction equation

HRID 2051913 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[CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN(C)P(N(C)C)(N(C)C)=O>O>[O:17]([CH2:16][CH2:15][CH2:14][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:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 68522Benzene, (3-bromopropoxy)-

Product 1

HCID 20378391HCID 20378391, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 33 g of ethyl p-aminobenzoate, 21.5 g of 3-bromopropylphenyl ether and 100 ml of hexamethylphosphoramide is heated at 100°-110° C. in an oil bath for 20 hours. The mixture is chilled, diluted with 50 ml of water, chilled and filtered. The solid is washed with ethanol-water (1:1) and with water to give yellow crystals, mp 73°-74° C.

Workup

  1. temperatureis heated at 100°-110° C. in an oil bath for 20 hours
  2. temperatureThe mixture is chilled
  3. temperaturechilled
  4. filtrationfiltered
  5. washThe solid is washed with ethanol-water (1:1) and with water
  6. customto give yellow crystals, mp 73°-74° C.

Sources & evidence

ORD record
ord-c0e64f51e3734172a142fa3a0602ce30
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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