Sulfuric Acid → HCID 21568606, compound

HRID 1579542Notes

Reaction equation

HRID 1579542 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([C:6]([C:8]2[CH:32]=[CH:31][CH:30]=[CH:29][C:9]=2[C:10]([N:12]([CH2:15][CH:16]([CH3:28])[NH:17]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:13][CH3:14])=O)=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O>>[ClH:1].[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([C:6](=[O:7])[C:8]2[CH:32]=[CH:31][CH:30]=[CH:29][C:9]=2[C:10]2[N:12]([CH2:13][CH3:14])[CH2:15][CH:16]([CH3:28])[N:17]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 53743771HCID 53743771, compound

Product 1

HCID 21568606HCID 21568606, compound

Procedure

Forty grams of 2-(p-chlorobenzoyl)-N-[2-methyl-2-(p-toluenesulfonamido)ethyl]-N-ethylbenzamide and 100 ml. of 90% (v/v) sulfuric acid were mixed together and heated in a steam bath for 45 minutes. After standing at room temperature 21 hours, the solution was quenched with 500 ml. of ice water. The mixture was extracted with dichloromethane. The aqueous portion was cooled and made basic with 50% sodium hydroxide solution. The mixture was extracted with ethyl acetate. The ethyl acetate portion was extracted with water then dried over magnesium sulfate. The solvent was removed in vacuo. The residue was dissolved in diethyl ether and treated with hydrogen chloride. The solid was separated and recrystallized from ethanol-ethyl acetate to obtain 4'-chloro-2-(1-ethyl-4-methyl-2-imidazolin-2-yl)benzophenone hydrochloride, m.p. 212°-214°C.

Workup

  1. temperatureheated in a steam bath for 45 minutes
  2. customthe solution was quenched with 500 ml
  3. extractionThe mixture was extracted with dichloromethane
  4. temperatureThe aqueous portion was cooled
  5. extractionThe mixture was extracted with ethyl acetate
  6. extractionThe ethyl acetate portion was extracted with water
  7. dry with materialthen dried over magnesium sulfate
  8. customThe solvent was removed in vacuo
  9. dissolutionThe residue was dissolved in diethyl ether
  10. additiontreated with hydrogen chloride
  11. customThe solid was separated
  12. customrecrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-b3eead175a204a81b8cc38de18bb9c8a
Source dataset
uspto-grants-1976_01
Patent number
US03931218

Reaction notes

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