Benzocaine → HCID 903766, compound

HRID 485250Notes

Reaction equation

HRID 485250 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([NH2:12])=[CH:10][CH:11]=1)=[O:5].C(N(CC)CC)C.CCOCC.[CH3:25][O:26][C:27]1[CH:37]=[CH:36][C:30]([CH2:31][CH2:32][C:33](Cl)=[O:34])=[CH:29][CH:28]=1>ClCCl>[CH3:25][O:26][C:27]1[CH:37]=[CH:36][C:30]([CH2:31][CH2:32][C:33]([NH:12][C:9]2[CH:8]=[CH:7][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:11][CH:10]=2)=[O:34])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 2337BenzocaineHCID 3283Diethyl Ether2×HCID 8471TriethylamineHCID 109324413-(4-Methoxyphenyl)propionyl chloride

Product 1

HCID 903766HCID 903766, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 13.73 g. of benzocaine and 11.56 ml. of triethylamine in 100 ml. of ether is slowly added to a stirred solution of 15 g. of p-methoxyhydrocinnamoyl chloride in 100 ml. of ether. The mixture is stirred overnight, 250 ml. of dichloromethane are added, and the mixture is extracted with 200 ml. of water, then 200 ml. of 10% hydrochloric acid, dried over magnesium sulfate, and evaporated to yield a solid. This solid is crystallized from 200 ml. of toluene, giving 21.4 g. of the desired product as white crystals, m.p. 134°-135.5° C.

Workup

  1. extractionthe mixture is extracted with 200 ml
  2. dry with materialof 10% hydrochloric acid, dried over magnesium sulfate
  3. customevaporated
  4. customto yield a solid
  5. customThis solid is crystallized from 200 ml
  6. customof toluene, giving 21.4 g

Sources & evidence

ORD record
ord-fdc290e6cb2e41efb1da6384d46dcdfa
Source dataset
uspto-grants-1985_08
Patent number
US04536346

Reaction notes

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