Benzocaine → HCID 20378382, compound

HRID 2051907Notes

Reaction equation

HRID 2051907 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.CS(O[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=O)=O.CN(C)P(N(C)C)(N(C)C)=O>C(O)C.O>[O:29]([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][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:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 20378400HCID 20378400, compound

Product 1

HCID 20378382HCID 20378382, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 16.5 g of ethyl p-aminobenzoate, 10.3 g of 11-phenoxy-1-undecanol O-methanesulfonate and 50 ml of hexamethylphosphoramide is heated at 100°-110° C. for 20 hours, chilled, and diluted with 30 ml of ethanol and 10 ml of water. Chilling and filtering gives a solid which is washed with ethanol-water (1:1) and with water to give yellow crystals, mp 83°-87° C. Recrystallization from ethanol gives yellow needles, mp 89°-90° C.

Workup

  1. temperatureis heated at 100°-110° C. for 20 hours
  2. temperaturechilled
  3. temperatureChilling
  4. filtrationfiltering
  5. customgives a solid which
  6. washis washed with ethanol-water (1:1) and with water
  7. customto give yellow crystals, mp 83°-87° C
  8. customRecrystallization from ethanol
  9. customgives yellow needles, mp 89°-90° C.

Sources & evidence

ORD record
ord-f03de43d8f4f47d7bfc33fdc984fc23d
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

Loading…