Sulfuric Acid → HCID 21568637, compound

HRID 1579536Notes

Reaction equation

HRID 1579536 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]([CH2:16][CH2:17][NH:18]S(C2C=CC(C)=CC=2)(=O)=O)[CH:13]([CH3:15])[CH3:14])=O)=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O>>[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]([CH:13]([CH3:15])[CH3:14])[CH2:16][CH2:17][N:18]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 54339724HCID 54339724, compound

Product 1

HCID 21568637HCID 21568637, compound

Procedure

Eighteen grams of 2-(p-chlorobenzoyl)-N-[2(p-toluenesulfonamido)ethyl]N-isopropylbenzamide and 65 ml. of 90% (v/v) sulfuric acid were mixed together and heated in a steam bath for thirty minutes. The solution was left standing at room temperature for 17 hours. The mixture was quenched with 800 ml. of ice water and extracted with ethyl acetate. The aqueous portion was cooled and made basic with 50% sodium hydroxide solution. The mixture was extracted with ethyl acetate. The organic portion was extracted with water then dried over magnesium sulfate. The solvent was removed in vacuo. The residue was recrystallized from ethyl acetate-hexane to obtain 4'-chloro-2-(1-isopropyl-2-imidazolin-2-yl)benzophenone, m.p. 114°-117°C. Anal. Calc'd for C19H19N2ClO: C, 69.82; H, 5.86; N, 8.57; Cl, 10,85. Found: C, 69.62; H, 6.05; N, 8.35; Cl, 10.87.

Workup

  1. temperatureheated in a steam bath for thirty minutes
  2. waitThe solution was left
  3. customThe mixture was quenched with 800 ml
  4. extractionof ice water and extracted with ethyl acetate
  5. temperatureThe aqueous portion was cooled
  6. extractionThe mixture was extracted with ethyl acetate
  7. extractionThe organic portion was extracted with water
  8. dry with materialthen dried over magnesium sulfate
  9. customThe solvent was removed in vacuo
  10. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ae32be4cc45c413cb734e3f20f1a22f8
Source dataset
uspto-grants-1976_01
Patent number
US03931218

Reaction notes

Loading…