Ethylene Glycol → HCID 20516512, compound

HRID 1902336Notes

Reaction equation

HRID 1902336 reaction equation
Cl.[NH2:2][C:3]1[C:11]([CH2:12][N:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][CH3:15])=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]=1[Br:22].N1C=CC=CC=1.[OH-].[Na+].[CH2:31]([OH:34])[CH2:32][OH:33]>O>[NH2:2][C:3]1[C:11]([CH2:12][N:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][CH3:15])=[CH:10][C:6]([C:7]([O:33][CH2:32][CH2:31][OH:34])=[O:8])=[CH:5][C:4]=1[Br:22]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1049PyridineHCID 14798Sodium HydroxideHCID 86738669HCID 86738669, compound

Product 1

HCID 20516512HCID 20516512, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

41 gm (0.1 mol) of 4-amino-3-bromo-5-(N-ethylcyclohexylaminomethyl)-benzoyl chloride hydrochloride were dissolved in 250 ml of ethylene glycol, and after addition of 17 gm (0.22 mol) of pyridine the solution was heated to 105° C. for one hour. After cooling to room temperature, the mixture was diluted with 1 liter of water. After addition of aqueous sodium hydroxide the mixture was extracted with ether, the ether extract was dried over sodium sulfate and evaporated to dryness. The residue was chromatographed on silicagel (eluant: ethyl acetate). After evaporation of the eluate, a resin was obtained which was converted into crystals by trituration with petroleum ether. The crystals obtained were recrystallized from ethanol.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionwas extracted with ether
  3. extractionthe ether extract
  4. dry with materialwas dried over sodium sulfate
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silicagel (eluant: ethyl acetate)
  7. customAfter evaporation of the eluate
  8. customa resin was obtained which
  9. customThe crystals obtained
  10. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-10078f21d98d48929a52fc3a7773012a
Source dataset
uspto-grants-1982_12
Patent number
US04362738

Reaction notes

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