Sulfuric Acid → HCID 21568625, compound

HRID 1579540Notes

Reaction equation

HRID 1579540 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([C:6]([C:8]2[CH:33]=[CH:32][CH:31]=[CH:30][C:9]=2[C:10]([N:12]([C:15]([CH3:29])([CH3:28])[CH2:16][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>>[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([C:6](=[O:7])[C:8]2[CH:33]=[CH:32][CH:31]=[CH:30][C:9]=2[C:10]2[N:12]([CH2:13][CH3:14])[C:15]([CH3:29])([CH3:28])[CH2:16][N:17]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 54186951HCID 54186951, compound

Product 1

HCID 21568625HCID 21568625, compound

Procedure

One-hundred-ninety grams of 2-(p-chlorobenzoyl)-N-[1,1-dimethyl-2-(p-toluenesulfonamido)ethyl]-N-ethyl benzamide and 400 ml. of 90% (v/v) sulfuric acid were mixed together and heated in a steam bath for 45 minutes. The solution was left at room temperature for 21 hours, then quenched with 3 volumes 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 dichloromethane. This solvent was removed in vacuo. The residue crystallized on standing overnight. A portion was recrystallized from diethyl ether-hexane to obtain 4'-chloro-2-(1-ethyl-5,5-dimethyl-2-imidazolin-2-yl)benzophenone, m.p. 85°-87°C.

Workup

  1. temperatureheated in a steam bath for 45 minutes
  2. customquenched with 3 volumes of ice water
  3. extractionThe mixture was extracted with dichloromethane
  4. temperatureThe aqueous portion was cooled
  5. extractionThe mixture was extracted with dichloromethane
  6. customThis solvent was removed in vacuo
  7. customThe residue crystallized
  8. waiton standing overnight
  9. customA portion was recrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-a387849a27214e4d90a9bb45e5d6f9aa
Source dataset
uspto-grants-1976_01
Patent number
US03931218

Reaction notes

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