Benzocaine → HCID 13503404, compound

HRID 485255Notes

Reaction equation

HRID 485255 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]([OH:11])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)(=O)=O.ClC1C=CC(C(C2C=CC(Cl)=CC=2)C(Cl)=O)=CC=1.[CH3:42][CH2:43][O:44][C:45]([C:47]1[CH:48]=[CH:49][C:50]([NH2:53])=[CH:51][CH:52]=1)=[O:46]>C1C=CC=CC=1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:9]([NH:53][C:50]2[CH:49]=[CH:48][C:47]([C:45]([O:44][CH2:43][CH3:42])=[O:46])=[CH:52][CH:51]=2)=[O:11])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 2337BenzocaineHCID 6730Bis(4-chlorophenyl)acetic acidHCID 24648Sulfuryl chlorideHCID 12497069HCID 12497069, compound

Product 1

HCID 13503404HCID 13503404, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 23.55 g. of bis(p-chlorophenyl)acetic acid in 250 ml. of benzene is added dropwise 33.1 g. of sulfonyl chloride. The mixture is refluxed 5 hours, the solvent is evaporated, and the residue is evaporated from three 250 ml. portions of benzene, giving 26.06 g. of bis(p-chlorophenyl)acetyl chloride as an oil. To this oil is added a solution of 27.7 g. of benzocaine. The mixture is stirred overnight, filtered, washed with 200 ml. each of 10% hydrochloric acid, saturated sodium bicarbonate solution, water, and brine, dried over magnesium sulfate, and evaporated. The residue is crystallized twice from 200 ml. of ethanol, giving 25.76 g. of the desired product as colorless needles, m.p. 171°-172° C.

Workup

  1. temperatureThe mixture is refluxed 5 hours
  2. customthe solvent is evaporated
  3. customthe residue is evaporated from three 250 ml
  4. customportions of benzene, giving 26.06 g
  5. additionTo this oil is added a solution of 27.7 g
  6. filtrationfiltered
  7. washwashed with 200 ml
  8. dry with materialeach of 10% hydrochloric acid, saturated sodium bicarbonate solution, water, and brine, dried over magnesium sulfate
  9. customevaporated
  10. customThe residue is crystallized twice from 200 ml
  11. customof ethanol, giving 25.76 g

Sources & evidence

ORD record
ord-f189e3284257475f9bdd9d06d8e1ed8f
Source dataset
uspto-grants-1985_08
Patent number
US04536346

Reaction notes

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