Benzocaine → Ethyl 4-{[3-(4-chlorophenoxy)propyl]amino}benzoate

HRID 2051921Notes

Reaction equation

HRID 2051921 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][O:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)(=O)=O.CN(C)P(N(C)C)(N(C)C)=O>O>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][CH2:19][CH2:18][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:23][CH:24]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 10967402HCID 10967402, compound

Product 1

HCID 20378386Ethyl 4-{[3-(4-chlorophenoxy)propyl]amino}benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 17.1 g. of ethyl p-aminobenzoate, 14.6 g. of 3-(4-chlorophenoxy)-1-propanol O-methanesulfonate and 100 ml. of hexamethylphosphoramide is heated at 110°-115° C. for 16 hours. The solution is diluted with 100 ml. of water, allowed to cool and is filtered to give 12.5 g. of solid. Recrystallization from cyclohexane gives 7.8 g. of yellow needles. Chromatography over silica gel gives 6.8 g. of product as white crystals, m.p. 87°-88° C.

Workup

  1. additionA mixture of 17.1 g
  2. additionThe solution is diluted with 100 ml
  3. temperatureto cool
  4. filtrationis filtered
  5. customto give 12.5 g
  6. customRecrystallization from cyclohexane
  7. customgives 7.8 g
  8. customChromatography over silica gel gives 6.8 g

Sources & evidence

ORD record
ord-4c8f67b82d9d4c3e96bdccf5090e80c8
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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